Substituted benzoylpyrazoles

ABSTRACT

The invention relates to novel substituted benzoylpyrazoles of the formula (I),  
                 
 
     in which n, A, R 1 , R 2 , R 3  R 4 , Y, and Z are as defined herein, and also to processes for their preparation and to their use as herbicides.

[0001] The invention relates to novel substituted benzoylpyrazoles, toprocesses for their preparation and to their use as herbicides.

[0002] It is already known that certain substituted benzoylpyrazoleshave herbicidal properties (cf. EP-A-352543, WO-A-96/26206,WO-A-97/35850, WO-A-97/41105, WO-A-97/41116, WO-A-97/41117,WO-A-97/4118, WO-A-97/46530, WO-A-98/28981, WO-A-98/31681,WO-A-98/31682, WO-A-99/07697). However, the activity of these compoundsis not entirely satisfactory.

[0003] This invention now provides the novel substitutedbenzoylpyrazoles of the general formula (I)

[0004] in which

[0005] n represents the numbers 0, 1, 2 or 3,

[0006] A represents a single bond or represents alkanediyl (alkylene),

[0007] R¹ represents in each case optionally substituted alkyl, alkenyl,alkinyl or cycloalkyl,

[0008] R² represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen,or represents in each case optionally substituted alkyl, alkoxy,alkylthio, alkoxycarbonyl or cycloalkyl,

[0009] R³ represents hydrogen, nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, halogen, or represents in each case optionallysubstituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl,alkylamino, dialkylamino or dialkylaminosulfonyl,

[0010] R⁴ represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl,halogen, or represents in each case optionally substituted alkyl,alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino,dialkylamino or dialkylaminosulfonyl,

[0011] Y represents hydrogen or represents in each case optionallysubstituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl,alkylaminocarbonyl, dialkylaminocarbonyl, alkenyl, alkenylcarbonyl,alkenylsulfonyl, alkinyl, alkinylcarbonyl, cycloalkyl,cycloalkylcarbonyl, cycloalkylalkyl, phenylcarbonyl, phenylsulfonyl,phenylalkyl or phenylcarbonylalkyl, and

[0012] Z represents an optionally substituted 4- to 12-memberedsaturated or unsaturated monocyclic or bicyclic heterocyclic groupingwhich contains 1 to 4 heteroatoms (up to 4 nitrogen atoms andoptionally—alternatively or additionally—one oxygen atom or one sulfuratom, or an SO grouping or an SO₂ grouping) and which additionallycontains one to three oxo groups (C═O) and/or thioxo groups (C═S) ascomponent of the heterocycle,

[0013] including all possible tautomeric forms of the compounds of thegeneral formula (I) and the possible salts of the compounds of thegeneral formula (I).

[0014] In the definitions, the hydrocarbon chains, such as alkyl oralkanediyl, are in each case straight-chain or branched—including incombination with heteroatoms, such as in alkoxy.

[0015] n preferably represents the numbers 0, 1 or 2.

[0016] A preferably represents a single bond or represents alkanediyl(alkylene) having 1 to 4 carbon atoms.

[0017] R¹ preferably represents optionally cyano, carboxyl-, carbamoyl-,halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl-, C₁-C₄-alkoxy-carbonyl-,C₁-C₄-alkylthio-, C₁-C₄-alkylsulfinyl- orC₁-C₄-alkylsulfonyl-substituted alkyl having 1 to 6 carbon atoms,represents in each case optionally cyano-, carboxyl-, carbamoyl-,halogen- or C₁-C₄-alkoxy-carbonyl-substituted alkenyl or alkinyl havingin each case 2 to 6 carbon atoms, or represents optionally cyano-,carboxyl-, carbamoyl-, halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms.

[0018] R² preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, halogen, represents in each case optionally cyano-,halogen- or C₁-₄-alkoxy-substituted alkyl, alkoxy or alkoxycarbonylhaving in each case up to 6 carbon atoms, represents optionallyhalogen-substituted alkylthio having 1 to 6 carbon atoms, or representsoptionally cyano-, halogen- or C₁-₄-alkyl-substituted cycloalkyl having3 to 6 carbon atoms.

[0019] R³ preferably represents hydrogen, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, halogen, represents in each case optionallyhalogen, C₁-₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulfinyl- orC₁-C₄-alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinylor alkylsulfonyl having in each case up to 4 carbon atoms in the alkylgroups, or represents alkylamino, dialkylamino or dialkylaminosulfonylhaving in each case up to 4 carbon atoms in the alkyl groups.

[0020] R⁴ preferably represents nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, halogen, represents in each case optionally halogen-,C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulfinyl- orC₁-C₄-alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinylor alkylsulfonyl having in each case up to 4 carbon atoms in the alkylgroups, or represents alkylamino, dialkylamino or dialkylaminosulfonylhaving in each case up to 4 carbon atoms in the alkyl groups.

[0021] Y preferably represents hydrogen, represents in each caseoptionally cyano-, carboxyl-, carbamoyl-, halogen- orC₁-C₄-alkoxycarbonyl-substituted alkyl, alkylcarbonyl or alkoxycarbonylhaving in each case up to 6 carbon atoms, represents in each caseoptionally halogen-substituted alkylsulfonyl, alkyl-aminocarbonyl ordialkylaminocarbonyl having in each case up to 6 carbon atoms in thealkyl groups, represents in each case optionally cyano-, carboxyl-,carbamoyl-, halogen- or C₁-C₄-alkoxy-carbonyl-substituted alkenyl,alkenylcarbonyl, alkinyl or alkinylcarbonyl having in each case 2 to 6carbon atoms, represents optionally halogen-substituted alkenylsulfonylhaving up to 6 carbon atoms represents in each case optionally cyano-,halogen- or C₁-C₄-alkyl-substituted cycloalkyl, cycloalkylcarbonyl orcycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl groups and optionally 1 to 3 carbon atoms in the alkylmoiety, or represents in each case optionally nitro-, cyano-, carboxyl-,carbamoyl-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-or C₁-C₄-halogenoalkoxy-substituted phenylcarbonyl, phenylsulfonyl,phenyl-C₁-C₄-alkyl or phenylcarbonyl-C₁-C₄-alkyl.

[0022] Z preferably represents one of the heterocyclic groupings below

[0023] in which in each case the broken bond is a single bond or adouble bond,

[0024] Q represents oxygen or sulfur,

[0025] R⁵ represents hydrogen, hydroxyl, mercapto, cyano, halogen,represents in each case optionally cyano-, halogen-, C₁-C₄-alkoxy-,C₁-C₄-alkylthio-, C₁-C₄-alkylsulfinyl- or C₁-C₄-alkylsulfonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio,alkylsulfinyl or alkylsulfonyl having in each case up to 6 carbon atomsin the alkyl groups, represents propadienylthio, represents in each caseoptionally halogen-substituted alkylamino or dialkylamino having in eachcase up to 6 carbon atoms in the alkyl groups, represents in each caseoptionally halogen-substituted alkenyl, alkinyl, alkenyloxy, alkenylthioor alkenylamino having in each case up to 6 carbon atoms in the alkenylor alkinyl groups, represents in each case optionallyhalogen-substituted cycloalkyl, cycloalkyloxy, cycloalkylathio,cycloalkyl amino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthioor cycloalkylalkylamino having in each case 3 to 6 carbon atoms in thecycloalkyl groups and optionally up to 4 carbon atoms in the alkylmoiety, represents in each case optionally halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino,benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino,piperidino or morpholino, or—if two adjacent radicals R⁵ and R⁵ arelocated on a double bond—together with the adjacent radical R⁵ alsorepresents a benzo grouping, and

[0026] R⁶ represents hydrogen, hydroxyl, amino, alkylideneamino havingup to 4 carbon atoms, represents in each case optionally halogen- orC₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylamino, dialkylamino oralkanoylamino having in each case up to 6 carbon atoms in the alkylgroups, represents in each case optionally halogen-substituted alkenyl,alkinyl or alkenyloxy having in each case up to 6 carbon atoms in thealkenyl or alkinyl groups, represents in each case optionallyhalogen-substituted cycloalkyl, cycloalkylalkyl or cycloalkylaminohaving in each case 3 to 6 carbon atoms in the cycloalkyl groups andoptionally up to 3 carbon atoms in the alkyl moiety, or represents ineach case optionally halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substitutedphenyl or benzyl, or together with an adjacent radical R⁵ or R⁶represents optionally halogen- or C₁-C₄-alkyl-substituted alkanediylhaving 3 to 5 carbon atoms,

[0027] where the individual radicals R⁵ and R⁶—if a plurality of theseare attached to the same heterocyclic groupings, may have identical ordifferent meanings within the scope of the above definition.

[0028] Q preferably represents oxygen.

[0029] R⁵ preferably represents hydrogen, hydroxyl, mercapto, cyano,fluorine, chlorine, bromine, iodine, represents in each case optionallyfluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- ort-butoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- ort-butylthio-, methylsulfinyl-, ethylsulfinyl-, n- or i-propylsulfinyl-,methylsulfonyl-, ethylsulfonyl-, n- or i-propylsulfonyl-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy,n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl,n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- ori-propylsulfonyl, represents methylamino, ethylamino, n- ori-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino,di-n-propylamino or di-i-propylamino, represents in each case optionallyfluorine- and/or chlorine-substituted ethenyl, propenyl, butenyl,ethinyl, propinyl, butinyl, propenyloxy, butenyloxy, propenylthio,butenylthio, propenylamino or butenylamino, represents in each caseoptionally fluorine- and/or chlorine-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy,cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio,cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino,cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy,cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio,cyclohexylmethylthio, cyclopropylmethyl amino, cyclobutylmethylamino,cyclopentylmethylamino or cyclohexylmethylamino, represents in each caseoptionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, methoxy-, ethoxy-, n- or i-propoxy-substitutedphenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy,benzylthio or benzylamino, represents pyrrolidino, piperidino ormorpholino, or—if two radicals R⁵ and R⁵ are located on a doublebond—together with the adjacent radical R⁵ also represents a benzogrouping.

[0030] R⁶ preferably represents hydrogen, hydroxyl, amino, represents ineach case optionally fluorine- and/or chlorine-, methoxy- orethoxy-substituted, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl,methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino ordimethylamino, represents in each case optionally fluorine- and/orchlorine-substituted ethenyl, propenyl, ethinyl, propinyl orpropenyloxy, represents in each case optionally fluorine- and/orchlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, or represents in each case optionally fluorine-,chlorine-, methyl-, ethyl-, n- or i-propyl, n-, i-, s- or t-butyl-,methoxy-, ethoxy-, n- or i-propoxy-substituted phenyl or benzyl, ortogether with an adjacent radical R⁵ or R⁶ represents in each caseoptionally methyl- and/or ethyl-substituted propane-1,3-diyl(trimethylene), butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl(pentamethylene).

[0031] n particularly preferably represents the numbers 0 or 1.

[0032] A particularly preferably represents a single bond, methylene,ethylidene (ethane-1,1-diyl) or dimethylene (ethane-1,2-diyl).

[0033] R¹ particularly preferably represents in each case optionallyfluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-,ethylthio-, n- or i-propylthio-, methylsulfinyl-, ethylsulfinyl-, n- ori-propylsulfinyl-, methylsulfonyl-, ethylsulfonyl-, n- ori-propylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, represents in each case optionally fluorine-, chlorine- orbromine-substituted propenyl, butenyl, propinyl or butinyl, orrepresents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl.

[0034] R² particularly preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, represents in each case optionally cyano-, fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, represents ineach case optionally fluorine- and/or chlorine-substituted methylthio,ethylthio, n- or i-propylthio, or represents in each case optionallycyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0035] R³ particularly preferably represents hydrogen, nitro, cyano,carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine,represents in each case optionally fluorine- and/or chlorine-, methoxy-,ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- orethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, represents in each case optionally fluorine- and/or chlorine-,methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- ori-propoxy, represents in each case optionally fluorine- and/orchlorine-substituted methylthio, ethylthio, n- or i-propylthio,methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl,ethylsulfonyl, n- or i-propylsulfonyl, or represents methylamino,ethylamino, n- or i-propylamino, dimethylamino, diethylamino,dimethylaminosulfonyl or diethylaminosulfonyl.

[0036] R⁴ particularly preferably represents nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, represents ineach case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n-or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- orethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, represents in each case optionally fluorine- and/or chlorine-,methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- ori-propoxy, represents in each case optionally fluorine- and/orchlorine-substituted methylthio, ethylthio, n- or i-propylthio,methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl,ethylsulfonyl, n- or i-propylsulfonyl, or represents methylamino,ethylamino, n- or i-propylamino, dimethylamino, diethylamino,dimethylaminosulfonyl or diethylaminosulfonyl.

[0037] R⁵ particularly preferably represents hydrogen, hydroxyl,chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl,difluoroethyl, dichloroethyl, fluoro-n-propyl, fluoro-i-propyl,chloro-n-propyl chloro-i-propyl, methoxymethyl, ethoxymethyl,methoxyethyl, ethoxyethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s-or t-butoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy,trifluoroethoxy, trichloroethoxy, chlorofluoroethoxy,chlorodifluoroethoxy, fluorodichloroethoxy, methylthio, ethylthio, n- ori-propylthio, fluoroethylthio, chloroethylthio, difluoroethylthio,dichloroethylthio, chlorofluoroethylthio, chlorodifluoroethylthio,fluorodichloroethylthio, methylsulfinyl, ethylsulfinyl, n- ori-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl,dimethylamino, propenylthio, butenylthio, -propinylthio, butinylthio,cyclopropyl, cyclopropylmethyl, cyclopropylmethoxy, phenyl or phenoxy.

[0038] R⁶ particularly preferably represents amino, methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylamino,dimethylamino, cyclopropyl or cyclopropylmethyl, or together with R⁵represents propane-1,3-diyl (trimethylene), butane-1,4-diyl(tetramethylene) or pentane-1,5-diyl (pentamethylene).

[0039] Y particularly preferably represents hydrogen, represents in eachcase optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, acetyl, propionyl, n-or i-butyroyl, methoxycarbonyl or ethoxycarbonyl, represents in eachcase optionally fluorine-, chlorine- and/or bromine-substitutedmethylsulfonyl-, ethylsulfonyl-, n- or i-propylsulfonyl-, n-, i-, s- ort-butylsulfonyl-, methylaminocarbonyl, ethylaminocarbonyl, n- ori-propylaminocarbonyl, dimethylaminocarbonyl or diethylaminocarbonyl,represents in each case optionally fluorine-, chlorine- orbromine-substituted propenyl, butenyl, propenylcarbonyl,butenylcarbonyl, propenylsulfonyl, butenylsulfonyl, propinyl, butinyl,propinylcarbonyl or butinylcarbonyl, represents in each case optionallycyano-, fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylcarbonyl,cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, difluoromethoxy- or trifluoromethoxy-substitutedphenylcarbonyl, phenylsulfonyl, benzyl or phenylcarbonylmethyl.

[0040] Z particularly preferably represents

[0041] n very particularly preferably represents 0.

[0042] A very particularly preferably represents a single bond orrepresents methylene.

[0043] R¹ very particularly preferably represents in each caseoptionally fluorine, chlorine-, methoxy-, ethoxy-, methylthio-,ethylthio-, methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- orethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, or represents optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl.

[0044] R² very particularly preferably represents hydrogen, cyano,carbarnoyl, fluorine, chlorine, bromine, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, represents in each caseoptionally fluorine- and/or chlorine-substituted methylthio, ethylthio,n- or i-propylthio, or reprcsents cyclopropyl.

[0045] R³ very particularly preferably represents hydrogen, nitro,cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl,trifluoromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl,methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy,trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl,methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl.

[0046] R⁴ particularly preferably represents nitro, cyano, fluorine,chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxymethyl,methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy,ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl,dimethylamino or dimethylaminosulfonyl.

[0047] R⁶ very particularly preferably represents methyl, cyclopropyl,dimethylamino, methoxy or ethoxy.

[0048] Y very particularly preferably represents hydrogen.

[0049] A most preferably represents methylene.

[0050] R¹ most preferably represents methyl or ethyl.

[0051] R² most preferably represents hydrogen or methyl.

[0052] R³ most preferably represents hydrogen, fluorine, chlorine,bromine, trifluoromethyl or methylsulfonyl.

[0053] R⁴ most preferably represents (2-)chlorine, (4-)chlorine,(6-)trifluoromethyl or (2-)methylsulfonyl.

[0054] Preference according to the invention is given to compounds ofthe formula (I) which contains a combination of the meanings listedabove as being preferred.

[0055] Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

[0056] Very particular preference is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing very particularly preferred.

[0057] Most preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being most preferred.

[0058] The present invention in particular provides the compounds of thegeneral formulae (IA), (IB) and (IC):

[0059] in which

[0060] n, A, Q, R¹, R², R³, R⁴, R⁵, R⁶ and Y are as defined above.

[0061] The invention preferably also provides sodium, potassium,magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium,di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium,tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulfonium, C₅- orC₆-Cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzylammonium salts ofcompounds of the formula (I), in which n, A, R¹, R², R³, R⁴, Y and Z areas defined above.

[0062] The abovementioned general or preferred radical definitions applyboth to the end products of the formula (I) and, correspondingly to thestarting materials or intermediates required in each case for thepreparation. These radical definitions can be combined with one anotheras desired, i.e. including combinations between the given preferredranges.

[0063] Examples of the compounds of the general formula (I) according tothe invention are given in the groups below.

[0064] Group 1

[0065] Here, R³, (R⁴)_(n), R⁵ and R⁶ have, for example, the meaningsgiven in the table below: R³ (Position) (R⁴)_(n) R⁵ R⁶ H — CF₃ CH₃ F —CF₃ CH₃ Cl — CF₃ CH₃ Br — CF₃ CH₃ I — CF₃ CH₃ NO₂ — CF₃ CH₃ CN — CF₃ CH₃CH₃ — CF₃ CH₃ OCH₃ — CF₃ CH₃ CF₃ — CF₃ CH₃ OCHF₂ — CF₃ CH₃ OCF₃ — CF₃CH₃ SO₂CH₃ — CF₃ CH₃ H — OCH₃ CH₃ F — OCH₃ CH₃ Cl — OCH₃ CH₃ Br — OCH₃CH₃ I — OCH₃ CH₃ NO₂ — OCH₃ CH₃ CN — OCH₃ CH₃ CH₃ — OCH₃ CH₃ OCH₃ — OCH₃CH₃ CF₃ — OCH₃ CH₃ OCHF₂ — OCH₃ CH₃ OCF₃ — OCH₃ CH₃ SO₂CH₃ — OCH₃ CH₃ H— SCH₃ CH₃ F — SCH₃ CH₃ Cl — SCH₃ CH₃ Br — SCH₃ CH₃ I — SCH₃ CH₃ NO₂ —SCH₃ CH₃ CN — SCH₃ CH₃ CH₃ — SCH₃ CH₃ OCH₃ — SCH₃ CH₃ CF₃ — SCH₃ CH₃OCHF₂ — SCH₃ CH₃ OCF₃ — SCH₃ CH₃ SO₂CH₃ — SCH₃ CH₃ H — OC₂H₅ CH₃ F —OC₂H₅ CH₃ Cl — OC₂H₅ CH₃ Br — OC₂H₅ CH₃ I — OC₂H₅ CH₃ NO₂ — OC₂H₅ CH₃ CN— OC₂H₅ CH₃ CH₃ — OC₂H₅ CH₃ OCH₃ — OC₂H₅ CH₃ CF₃ — OC₂H₅ CH₃ OCHF₂ —OC₂H₅ CH₃ OCF₃ — OC₂H₅ CH₃ SO₂CH₃ — OC₂H₅ CH₃ H — N(CH₃)₂ CH₃ F —N(CH₃)₂ CH₃ Cl — N(CH₃)₂ CH₃ Br — N(CH₃)₂ CH₃ I — N(CH₃)₂ CH₃ NO₂ —N(CH₃)₂ CH₃ CN — N(CH₃)₂ CH₃ CH₃ — N(CH₃)₂ CH₃ OCH₃ — N(CH₃)₂ CH₃ CF₃ —N(CH₃)₂ CH₃ OCHF₂ — N(CH₃)₂ CH₃ OCF₃ — N(CH₃)₂ CH₃ SO₂CH₃ — N(CH₃)₂ CH₃H — OCH₃

F — OCH₃

Cl — OCH₃

Br — OCH₃

I — OCH₃

NO₂ — OCH₃

CN — OCH₃

CH₃ — OCH₃

OCH₃ — OCH₃

CF₃ — OCH₃

OCHF₂ — OCH₃

OCF₃ — OCH₃

SO₂CH₃ — OCH₃

H (5-) Cl CF₃ CH₃ F (5-) Cl CH₃ CH₃ Cl (5-) Cl OCH₃ CH₃ Br (5-) Cl Br

Cl (5-) Cl CF₃ CH₃ NO₂ (5-) Cl CH₃ CH₃ Cl (5-) Cl SCH₃ CH₃ CH₃ (5-) ClCl CH₃ OCH₃ (5-) Cl OCH₃ CH₃ CF₃ (5-) Cl CF₃ CH₃ OCHF₂ (5-) Cl CH₃ CH₃OCF₃ (5-) Cl CH₃ CH₃ SO₂CH₃ (5-) Cl OCH₃ CH₃

[0066] Group 2

[0067] Here, R³, (R⁴)_(n), R⁵ and R⁶ have, for example, the meaningsgiven above in group 1.

[0068] Group 3

[0069] Here, R³, (R⁴)_(n), R⁵ and R⁶ have, for example, the meaningsgiven above in group 1.

[0070] Group 4

[0071] Here, R³, (R⁴)_(n), R⁵ and R⁶ have, for example, the meaningsgiven in the table below: R³ (Position) (R⁴)_(n) R⁵ R⁶ Cl (2-) Cl CF₃CH₃ Cl (2-) Cl SCH₃ CH₃ Cl (2-) Cl SC₂H₅ CH₃ Cl (2-) Cl SC₃H₇ CH₃ Cl(2-) Cl SC₃H₇-i CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl SCH═C═CH₂ CH₃ Cl (2-) Cl SCH₂CN CH₃ Cl (2-) Cl SCH₂CH₂CNCH₃ Cl (2-) Cl OCH₃ CH₃ Cl (2-) Cl OC₂H₅ CH₃ Cl (2-) Cl OC₃H₇ CH₃ Cl(2-) Cl OC₃H₇-i CH₃ Cl (2-) Cl OC₄H₉ CH₃ Cl (2-) Cl OCH₂CF₃ CH₃ Cl (2-)Cl

CH₃ Cl (2-) Cl OC₆H₅ CH₃ Cl (2-) Cl H CH₃ Cl (2-) Cl CH₃ CH₃ Cl (2-) ClC₂H₅ CH₃ Cl (2-) Cl C₃H₇ CH₃ Cl (2-) Cl C₃H₇-i CH₃ Cl (2-) Cl C₄H₉ CH₃Cl (2-) Cl C₄H₉-i CH₃ Cl (2-) Cl C₄H₉-s CH₃ Cl (2-) Cl C₄H₉-t CH₃ Cl(2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl CH═CHCH₃ CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl N(CH₃)₂ CH₃ Cl (2-) Cl

CH₃ Cl (2-) Cl Cl CH₃ Cl (2-) Cl Br CH₃ SO₂CH₃ (2-) Cl CF₃ CH₃ SO₂CH₃(2-) Cl SCH₃ CH₃ SO₂CH₃ (2-) Cl SC₂H₅ CH₃ SO₂CH₃ (2-) Cl SC₃H₇ CH₃SO₂CH₃ (2-) Cl SC₃H₇-i CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl SCH═C═CH₂ CH₃ SO₂CH₃ (2-) Cl SCH₂CN CH₃ SO₂CH₃ (2-)Cl SCH₂CH₂CN CH₃ SO₂CH₃ (2-) Cl OCH₃ CH₃ SO₂CH₃ (2-) Cl OC₂H₅ CH₃ SO₂CH₃(2-) Cl OC₃H₇ CH₃ SO₂CH₃ (2-) Cl OC₃H₇-i CH₃ SO₂CH₃ (2-) Cl OC₄H₉ CH₃SO₂CH₃ (2-) Cl OCH₂CF₃ CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl OC₆H₅ CH₃ SO₂CH₃ (2-) Cl H CH₃ SO₂CH₃ (2-) Cl CH₃ CH₃SO₂CH₃ (2-) Cl C₂H₅ CH₃ SO₂CH₃ (2-) Cl C₃H₇ CH₃ SO₂CH₃ (2-) Cl C₃H₇-iCH₃ SO₂CH₃ (2-) Cl C₄H₉ CH₃ SO₂CH₃ (2-) Cl C₄H₉-i CH₃ SO₂CH₃ (2-) ClC₄H₉-s CH₃ SO₂CH₃ (2-) Cl C₄H₉-t CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl CH═CHCH₃ CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl N(CH₃)₂ CH₃ SO₂CH₃ (2-) Cl

CH₃ SO₂CH₃ (2-) Cl Cl CH₃ SO₂CH₃ (2-) Cl Br CH₃ Cl (2-) SO₂CH₃ CF₃ CH₃Cl (2-) SO₂CH₃ SCH₃ CH₃ Cl (2-) SO₂CH₃ SC₂H₅ CH₃ Cl (2-) SO₂CH₃ SC₃H₇CH₃ Cl (2-) SO₂CH₃ SC₃H₇-i CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃ SCH═C═CH₂ CH₃ Cl (2-) SO₂CH₃ SCH₂CN CH₃ Cl (2-)SO₂CH₃ SCH₂CH₂CN CH₃ Cl (2-) SO₂CH₃ OCH₃ CH₃ Cl (2-) SO₂CH₃ OC₂H₅ CH₃ Cl(2-) SO₂CH₃ OC₃H₇ CH₃ Cl (2-) SO₂CH₃ OC₃H₇-i CH₃ Cl (2-) SO₂CH₃ OC₄H₉CH₃ Cl (2-) SO₂CH₃ OCH₂CF₃ CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃ OC₆H₅ CH₃ Cl (2-) SO₂CH₃ H CH₃ Cl (2-) SO₂CH₃ CH₃ CH₃Cl (2-) SO₂CH₃ C₂H₅ CH₃ Cl (2-) SO₂CH₃ C₃H₇ CH₃ Cl (2-) SO₂CH₃ C₃H₇-iCH₃ Cl (2-) SO₂CH₃ C₄H₉ CH₃ Cl (2-) SO₂CH₃ C₄H₉-i CH₃ Cl (2-) SO₂CH₃C₄H₉-s CH₃ Cl (2-) SO₂CH₃ C₄H₉-t CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃ CH═CHCH₃ CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃ N(CH₃)₂ CH₃ Cl (2-) SO₂CH₃

CH₃ Cl (2-) SO₂CH₃ Cl CH₃ Cl (2-) SO₂CH₃ Br CH₃ Cl (2-) Cl CF₃

Cl (2-) Cl SCH₃

Cl (2-) Cl SC₂H₅

Cl (2-) Cl SC₃H₇

Cl (2-) Cl SC₃H₇-i

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl SCH═C═CH₂

Cl (2-) Cl SCH₂CN

Cl (2-) Cl SCH₂CH₂CN

Cl (2-) Cl OCH₃

Cl (2-) Cl OC₂H₅

Cl (2-) Cl OC₃H₇

Cl (2-) Cl OC₃H₇-i

Cl (2-) Cl OC₄H₉

Cl (2-) Cl OCH₂CF₃

Cl (2-) Cl

Cl (2-) Cl OC₆H₅

Cl (2-) Cl H

Cl (2-) Cl CH₃

Cl (2-) Cl C₂H₅

Cl (2-) Cl C₃H₇

Cl (2-) Cl C₃H₇-i

Cl (2-) Cl C₄H₉

Cl (2-) Cl C₄H₉-i

Cl (2-) Cl C₄H₉-s

Cl (2-) Cl C₄H₉-t

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl CH═CHCH₃

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl

Cl (2-) Cl N(CH₃)₂

Cl (2-) Cl

Cl (2-) Cl Cl

Cl (2-) Cl Br

SO₂CH₃ (2-) Cl CF₃

SO₂CH₃ (2-) Cl SCH₃

SO₂CH₃ (2-) Cl SC₂H₅

SO₂CH₃ (2-) Cl SC₃H₇

SO₂CH₃ (2-) Cl SC₃H₇-i

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl SCH═C═CH₂

SO₂CH₃ (2-) Cl SCH₂CN

SO₂CH₃ (2-) Cl SCH₂CH₂CN

SO₂CH₃ (2-) Cl OCH₃

SO₂CH₃ (2-) Cl OC₂H₅

SO₂CH₃ (2-) Cl OC₃H₇

SO₂CH₃ (2-) Cl OC₃H₇-i

SO₂CH₃ (2-) Cl OC₄H₉

SO₂CH₃ (2-) Cl OCH₂CF₃

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl OC₆H₅

SO₂CH₃ (2-) Cl H

SO₂CH₃ (2-) Cl CH₃

SO₂CH₃ (2-) Cl C₂H₅

SO₂CH₃ (2-) Cl C₃H₇

SO₂CH₃ (2-) Cl C₃H₇-i

SO₂CH₃ (2-) Cl C₄H₉

SO₂CH₃ (2-) Cl C₄H₉-i

SO₂CH₃ (2-) Cl C₄H₉-s

SO₂CH₃ (2-) Cl C₄H₉-t

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl CH═CHCH₃

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl N(CH₃)₂

SO₂CH₃ (2-) Cl

SO₂CH₃ (2-) Cl Cl

SO₂CH₃ (2-) Cl Br

Cl (2-) SO₂CH₃ CF₃

Cl (2-) SO₂CH₃ SCH₃

Cl (2-) SO₂CH₃ SC₂H₅

Cl (2-) SO₂CH₃ SC₃H₇

Cl (2-) SO₂CH₃ SC₃H₇-i

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃ SCH═C═CH₂

Cl (2-) SO₂CH₃ SCH₂CN

Cl (2-) SO₂CH₃ SCH₂CH₂CN

Cl (2-) SO₂CH₃ OCH₃

Cl (2-) SO₂CH₃ OC₂H₅

Cl (2-) SO₂CH₃ OC₃H₇

Cl (2-) SO₂CH₃ OC₃H₇-i

Cl (2-) SO₂CH₃ OC₄H₉

Cl (2-) SO₂CH₃ OCH₂CF₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃ OC₆H₅

Cl (2-) SO₂CH₃ H

Cl (2-) SO₂CH₃ CH₃

Cl (2-) SO₂CH₃ C₂H₅

Cl (2-) SO₂CH₃ C₃H₇

Cl (2-) SO₂CH₃ C₃H₇-i

Cl (2-) SO₂CH₃ C₄H₉

Cl (2-) SO₂CH₃ C₄H₉-i

Cl (2-) SO₂CH₃ C₄H₉-s

Cl (2-) SO₂CH₃ C₄H₉-t

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃ CH═CHCH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃ N(CH₃)₂

Cl (2-) SO₂CH₃

Cl (2-) SO₂CH₃ Cl

Cl (2-) SO₂CH₃ Br

Cl (2-) Cl CF₃ N(CH₃)₂ Cl (2-) Cl SCH₃ N(CH₃)₂ Cl (2-) Cl SC₂H₅ N(CH₃)₂Cl (2-) Cl SC₃H₇ N(CH₃)₂ Cl (2-) Cl SC₃H₇-i N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl SCH═C═CH₂ N(CH₃)₂ Cl (2-) Cl SCH₂CN N(CH₃)₂ Cl (2-)Cl SCH₂CH₂CN N(CH₃)₂ Cl (2-) Cl OCH₃ N(CH₃)₂ Cl (2-) Cl OC₂H₅ N(CH₃)₂ Cl(2-) Cl OC₃H₇ N(CH₃)₂ Cl (2-) Cl OC₃H₇-i N(CH₃)₂ Cl (2-) Cl OC₄H₉N(CH₃)₂ Cl (2-) Cl OCH₂CF₃ N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl OC₆H₅ N(CH₃)₂ Cl (2-) Cl H N(CH₃)₂ Cl (2-) Cl CH₃N(CH₃)₂ Cl (2-) Cl C₂H₅ N(CH₃)₂ Cl (2-) Cl C₃H₇ N(CH₃)₂ Cl (2-) ClC₃H₇-i N(CH₃)₂ Cl (2-) Cl C₄H₉ N(CH₃)₂ Cl (2-) Cl C₄H₉-i N(CH₃)₂ Cl (2-)Cl C₄H₉-s N(CH₂)₂ Cl (2-) Cl C₄H₉-t N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl CH═CHCH₃ N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ N(CH₃)₂ Cl (2-) Cl

N(CH₃)₂ Cl (2-) Cl Cl N(CH₃)₂ Cl (2-) Cl Br N(CH₃)₂ SO₂CH₃ (2-) Cl CF₃N(CH₃)₂ SO₂CH₃ (2-) Cl SCH₃ N(CH₃)₂ SO₂CH₃ (2-) Cl SC₂H₅ N(CH₃)₂ SO₂CH₃(2-) Cl SC₃H₇ N(CH₃)₂ SO₂CH₃ (2-) Cl SC₃H₇-i N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl SCH═C═CH₂ N(CH₃)₂ SO₂CH₃ (2-) Cl SCH₂CN N(CH₃)₂SO₂CH₃ (2-) Cl SCH₂CH₂CN N(CH₃)₂ SO₂CH₃ (2-) Cl OCH₃ N(CH₃)₂ SO₂CH₃ (2-)Cl OC₂H₅ N(CH₃)₂ SO₂CH₃ (2-) Cl OC₃H₇ N(CH₃)₂ SO₂CH₃ (2-) Cl OC₃H₇-iN(CH₃)₂ SO₂CH₃ (2-) Cl OC₄H₉ N(CH₃)₂ SO₂CH₃ (2-) Cl OCH₂CF₃ N(CH₃)₂SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl OC₆H₅ N(CH₃)₂ SO₂CH₃ (2-) Cl H N(CH₃)₂ SO₂CH₃(2-) Cl CH₃ N(CH₃)₂ SO₂CH₃ (2-) Cl C₂H₅ N(CH₃)₂ SO₂CH₃ (2-) Cl C₃H₇N(CH₃)₂ SO₂CH₃ (2-) Cl C₃H₇-i N(CH₃)₂ SO₂CH₃ (2-) Cl C₄H₉ N(CH₃)₂ SO₂CH₃(2-) Cl C₄H₉-i N(CH₃)₂ SO₂CH₃ (2-) Cl C₄H₉-s N(CH₃)₂ SO₂CH₃ (2-) ClC₄H₉-t N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl CH═CHCH₃ N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ N(CH₃)₂ SO₂CH₃ (2-) Cl

N(CH₃)₂ SO₂CH₃ (2-) Cl Cl N(CH₃)₂ SO₂CH₃ (2-) Cl Br N(CH₃)₂ Cl (2-)SO₂CH₃ CF₃ N(CH₃)₂ Cl (2-) SO₂CH₃ SCH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ SC₂H₅N(CH₃)₂ Cl (2-) SO₂CH₃ SC₃H₇ N(CH₃)₂ Cl (2-) SO₂CH₃ SC₃H₇-i N(CH₃)₂ Cl(2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃ SCH═C═CH₂ N(CH₃)₂ Cl (2-) SO₂CH₃ SCH₂CN N(CH₃)₂Cl (2-) SO₂CH₃ SCH₂CH₂CN N(CH₃)₂ Cl (2-) SO₂CH₃ OCH₃ N(CH₃)₂ Cl (2-)SO₂CH₃ OC₂H₅ N(CH₃)₂ Cl (2-) SO₂CH₃ OC₃H₇ N(CH₃)₂ Cl (2-) SO₂CH₃ OC₃H₇-iN(CH₃)₂ Cl (2-) SO₂CH₃ OC₄H₉ N(CH₃)₂ Cl (2-) SO₂CH₃ OCH₂CF₃ N(CH₃)₂ Cl(2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃ OC₆H₅ N(CH₃)₂ Cl (2-) SO₂CH₃ H N(CH₃)₂ Cl (2-)SO₂CH₃ CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ C₂H₅ N(CH₃)₂ Cl (2-) SO₂CH₃ C₃H₇N(CH₃)₂ Cl (2-) SO₂CH₃ C₃H₇-i N(CH₃)₂ Cl (2-) SO₂CH₃ C₄H₉ N(CH₃)₂ Cl(2-) SO₂CH₃ C₄H₉-i N(CH₃)₂ Cl (2-) SO₂CH₃ C₄H₉-s N(CH₃)₂ Cl (2-) SO₂CH₃C₄H₉-t N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃ CH═CHCH₃ N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ N(CH₃)₂ Cl (2-) SO₂CH₃

N(CH₃)₂ Cl (2-) SO₂CH₃ Cl N(CH₃)₂ Cl (2-) SO₂CH₃ Br N(CH₃)₂ Cl (2-) ClCH₃ OCH₃ Cl (2-) Cl C₂H₅ OCH₃ Cl (2-) Cl C₃H₇ OCH₃ Cl (2-) Cl SCH₃ OCH₃Cl (2-) Cl SC₂H₅ OCH₃ Cl (2-) Cl OCH₃ OCH₃ Cl (2-) Cl OC₂H₅ OCH₃ Cl (2-)Cl CH₃ OC₂H₅ Cl (2-) Cl C₂H₅ OC₂H₅ Cl (2-) Cl C₃H₇ OC₂H₅ Cl (2-) Cl SCH₃OC₂H₅ Cl (2-) Cl SC₂H₅ OC₂H₅ Cl (2-) Cl OCH₃ OC₂H₅ Cl (2-) Cl OC₂H₅OC₂H₅ Cl (2-) SO₂CH₃ CH₃ OCH₃ Cl (2-) SO₂CH₃ C₂H₅ OCH₃ Cl (2-) SO₂CH₃C₃H₇ OCH₃ Cl (2-) SO₂CH₃ SCH₃ OCH₃ Cl (2-) SO₂CH₃ SC₂H₅ OCH₃ Cl (2-)SO₂CH₃ OCH₃ OCH₃ Cl (2-) SO₂CH₃ OC₂H₅ OCH₃ Cl (2-) SO₂CH₃ CH₃ OC₂H₅ Cl(2-) SO₂CH₃ C₂H₅ OC₂H₅ Cl (2-) SO₂CH₃ C₃H₇ OC₂H₅ Cl (2-) SO₂CH₃ SCH₃OC₂H₅ Cl (2-) SO₂CH₃ SC₂H₅ OC₂H₅ Cl (2-) SO₂CH₃ OCH₃ OC₂H₅ Cl (2-)SO₂CH₃ OC₂H₅ OC₂H₅ SO₂CH₃ (2-) Cl Cl OCH₃ SO₂CH₃ (2-) Cl Br OCH₃ SO₂CH₃(2-) Cl CH₃ OCH₃ SO₂CH₃ (2-) Cl C₂H₅ OCH₃ SO₂CH₃ (2-) Cl C₃H₇ OCH₃SO₂CH₃ (2-) Cl SCH₃ OCH₃ SO₂CH₃ (2-) Cl SC₂H₅ OCH₃ SO₂CH₃ (2-) Cl OCH₃OC₂H₅ SO₂CH₃ (2-) Cl OC₂H₅ OC₂H₅ SO₂CH₃ (2-) Cl CH₃ OC₂H₅ SO₂CH₃ (2-) ClC₂H₅ OC₂H₅ SO₂CH₃ (2-) Cl C₃H₇ OC₂H₅ SO₂CH₃ (2-) Cl SCH₃ OC₂H₅ SO₂CH₃(2-) Cl SC₂H₅ OC₂H₅ SO₂CH₃ (2-) Cl OCH₃ OC₂H₅

[0072] Group 5

[0073] Here, R³, (R⁴)_(n), R⁵ and R⁶ have, for example, the meaningsgiven above in group 4.

[0074] Group 6

[0075] Here, R³, (R⁴)_(n), R⁵ and R⁶ have, for example, the meaningsgiven above in group 4.

[0076] Group 7

[0077] Here, R³, (R⁴)_(n), R⁵ and R⁶ have, for example, the meaningsgiven in the table below: (Position) R³ (R⁴)_(n) R⁵ R⁶ H — CF₃ CH₃ F —CF₃ CH₃ Cl — CF₃ CH₃ Br — CF₃ CH₃

[0078] Group 8

[0079] Here, R³, (R⁴)_(n), R⁵ and R⁶ have, for example, the meaningsgiven above in group 7.

[0080] Group 9

[0081] Here, R³, (R⁴)_(n), R⁵ and R⁶ have, for example, the meaningsgiven above in group 7.

[0082] Group 10

[0083] Here, R³, (R⁴)_(n), R⁵ and R⁶ have, for example, the meaningsgiven in the table below: (Position) R³ (R⁴)_(n) R⁵ R⁶ H (2-) F CF₃ CH₃H (2-) Cl CF₃ CH₃ H (2-) Br CF₃ CH₃ H — CF₃ CH₃

[0084] Group 11

[0085] Here, R³, (R⁴)_(n), R⁵ and R⁶ have, for example, the meaningsgiven above in group 10.

[0086] Group 12

[0087] Here, R³, (R⁴)_(n), R⁵ and R⁶ have, for example, the meaningsgiven above in group 10.

[0088] The novel substituted benzoylpyrazoles of the general formular(I) have strong and selective herbicidal activity.

[0089] Novel substituted benzoylpyrazoles of the general formular (I)are obtained when

[0090] (a) pyrazoles of the general formula (II)

[0091] in which

[0092] R¹, R² and Y are as defined above,

[0093] are reacted with substituted benzoic acids of the general formula(III),

[0094] in which

[0095] n, A, R³, R⁴ and Z are as defined above,

[0096] in the presence of a dehydrating agent, if appropriate in thepresence of one or more reaction auxiliaries and if appropriate in thepresence of a diluent,

[0097] or when

[0098] (b) pyrazoles of the general formula (II)

[0099] in which

[0100] R¹, R² and Y are as defined above,

[0101] are reacted with substituted benzoic acid derivatives of thegeneral formula (IV)

[0102] in which

[0103] n, A, R³, R⁴ and Z are as defined above, and

[0104] X represents cyano, halogen or alkoxy,

[0105] or with corresponding carboxylic anhydrides—

[0106] if appropriate in the presence of one or more reactionauxiliaries and if appropriate in the presence of a diluent,

[0107] or when

[0108] (c) substituted benzoylpyrazoles of the general formula (Ia)

[0109] in which

[0110] n, A, R¹, R², R³, R⁴ and Z are as defined above,

[0111] are reacted with compounds of the general formula (V)

H—Y  (V)

[0112] in which

[0113] Y is as defined above, except for hydrogen,

[0114] or, if appropriate, with corresponding isocyanates orisothiocyanates—

[0115] if appropriate in the presence of one or more reactionauxiliaries and if appropriate in the presence of a diluent,

[0116] and, if appropriate, the resulting compounds of the formula (I)are subsequently subjected in a customary manner to electrophilic ornucleophilic and/or oxidation or reduction reactions within the scope ofthe definition of the substituents, or the compounds of the formula (I)are converted in a customary manner into salts.

[0117] The compounds of the formula (I) can be converted by customarymethods into other compounds of the formula (I) in accordance with theabove definition, for example by nucleophilic substitution (for exampleR⁵: Cl→OC₂H₅, SCH₃) or by oxidation (for example R⁵:CH₂SCH₃→CH₂S(O)CH₃).

[0118] Using, for example, 3-chloro-5-hydroxy-1-methyl-pyrazole and2-(3-carboxy-5-fluoro-benzyl)-5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-oneas starting materials, the course of the reaction in the process (a)according to the invention can be illustrated by the following formulascheme:

[0119] Using, for example, 3-cyano-5-hydroxy-1-ethyl-pyrazole and2-(3-methoxycarbonyl-5-chloro-benzyl)-4-ethyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-oneas starting materials, the course of the reaction in the process (b)according to the invention can be illustrated by the following formulascheme:

[0120] Using, for example,4-methyl-5-trifluoromethyl-2-[3-chloro-4-(1-ethyl-5-hydroxy-pyrazol-4-yl-carbonyl)-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-oneand benzoyl chloride as starting materials, the course of the reactionin the process (c) according to the invention can be illustrated by thefollowing formula scheme:

[0121] The formula (II) provides a general definition of the pyrazolesto be used as starting materials in the process (a) according to theinvention for preparing compounds of the general formula (I). In thegeneral formula (II), R¹, R² and Y preferably have those meanings whichhave already been mentioned above, in connection with the description ofthe compounds of the general formula (I) according to the invention, asbeing preferred, particularly preferred, very particularly preferred ormost preferred for R¹, R² and Y.

[0122] The starting materials of the general formula (II) are knownand/or can be prepared by processes known per se (cf. EP-A-240001).

[0123] The formula (III) provides a general definition of the benzoicacids further to be used as starting materials in the process (a)according to the invention. In the formula (III), n, A, R³, R⁴ and Zpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the formula (I)according to the invention, as being preferred, particularly preferred,very particularly preferred or most preferred for n, A, R³, R⁴ and Z.

[0124] Except for2-(5-carboxy-2,4-dichlorophenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one—alias2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-benzoicacid (CAS Reg. No. 90208-77-8) and2-(5-carboxy-2,4-dichloro-phenyl)-4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one—alias2,4-dichloro-5-(4,5-dihydro-3,4-dimethyl-5-oxo1H-1,2,4-triazol-1-yl)-benzoicacid (CAS Reg. No. 90208-76-7)—the starting materials of the generalformula (III) have hitherto not been disclosed in the literature.However, except for2-(5-carboxy-2,4-dichloro-phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-oneand 2-(5-carboxy-2,4-dichloro-phenyl)4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one (cf.JP-A-58225070—cited in Chem. Abstracts 100:209881, JP-A-02015069—citedin Chem. Abstracts 113:23929), they are the subject of an earlierapplication which, however, has not been published earlier (cf.DE-A-19833360).

[0125] The substituted benzoic acids of the general formula (III) areobtained when benzoic acid derivatives of the general formula (VI)

[0126] in which

[0127] n, A, R³ and R⁴ and Z are as defined above, and

[0128] X¹ represents cyano, carbamoyl, halogenocarbonyl oralkoxycarbonyl,

[0129] are reacted with water, if appropriate in the presence of ahydrolysis auxiliary, such as, for example, sulfuric acid, attemperatures between 50° C. and 120° C. (cf. the Preparation Examples).

[0130] The formula (IV) provides a general definition of the substitutedbenzoic acid derivatives to be used as starting materials in the process(b) according to the invention for preparing compounds of the generalformula (I). In the general formula (IV), n, A, R³, R⁴ and Z preferablyhave those meanings which have already been mentioned above, inconnection with the description of the compounds of the general formula(I) according to the invention, as being preferred, particularlypreferred, very particularly preferred or most preferred for n, A, R³,R⁴ and Z; X preferably represents cyano, fluorine, chlorine, bromine orC₁-C₄-alkoxy, in particular chlorine, methoxy or ethoxy.

[0131] The starting materials of the general formula (IV)—and theprecursors of the general formula (VI)—are known and/or can be preparedby processes known per se (cf. DE-A-3839480, DE-A-4239296, EP-A-597360,EP-A-609734, DE-A-4303676, EP-A-617026, DE-A4405614, US-A-5378681).

[0132] The formula (Ia) provides a general definition of the substitutedbenzoylpyrazoles to be used as starting materials in the process (c)according to the invention for preparing compounds of the generalformula (I). In the general formula (Ia), n, A, R¹, R², R³, R⁴ and Zpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the generalformula (I) according to the invention, as being preferred, particularlypreferred, very particularly preferred or most preferred for n, A, R¹,R², R³, R⁴ and Z.

[0133] The starting materials of the general formula (Ia) are novelcompounds according to the invention; they can be prepared by theprocesses (a) and (b) according to the invention.

[0134] The formula (V) provides a general definition of the compoundsfurther to be used as starting materials in the [lacuna] (c) accordingto the invention. In the general formula (V), Y preferably has thatmeaning which has already been mentioned above, in connection with thedescription of the compounds of the general formula (I) according to theinvention, as being preferred, particularly preferred, very particularlypreferred or most preferred for Y.

[0135] The starting materials of the general formula (V) are knownchemicals for synthesis.

[0136] The process (a) according to the invention for preparing thenovel substituted benzoylpyrazoles of the general formula (I) is carriedout using a dehydrating agent. Suitable dehydrating agents are thecustomary chemicals suitable for binding water.

[0137] Examples which may be mentioned are dicyclohexylcarbodiimide andcarbonyl-bis-imidazole.

[0138] A particularly suitable dehydrating agent which may be mentionedis dicyclohexylcarbodiimide.

[0139] The process (a) according to the invention for preparing thenovel substituted benzoylpyrazoles of the general formula (I) is, ifappropriate, carried out using a reaction auxiliary.

[0140] Examples of suitable reaction auxiliaries which may be mentionedare sodium cyanide, potassium cyanide, acetone cyanohydrin,2-cyano-2-(trimethylsilyloxy)-propane and trimethylsilyl cyanide.

[0141] A particularly suitable reaction auxiliary which may be mentionedis trimethylsilyl cyanide.

[0142] The process (b) according to the invention for preparing thenovel substituted benzoylpyrazoles of the general formula (I) is, ifappropriate, carried out using reaction auxilianes.

[0143] Examples of suitable reaction auxiliaries which may be mentionedare (conc.) sulfuric acid, zinc chloride, aluminum chloride, and boronfluoride.

[0144] The processes according to the invention for preparing the novelsubstituted benzoylpyrazoles of the general formula (I) are, ifappropriate, carried out using further reaction auxiliaries. Suitable(further) reaction auxiliaries for the processes according to theinvention are, in general, basic organic nitrogen compounds, such as,for example, trimethylamine, triethylamine, tripropylamine,tributylamine, ethyl-diisopropylamine, N,N-dimethyl-cyclohexylamine,dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethyl-aniline,N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-,2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethylpyridine,5-ethyl-2-methyl-pyridine, 4-dimethylanino-pyridine,N-methyl-piperidine, 1,4-diazabicyclo[2,2,2]-octane (DABCO),1,5-diazabicyclo[4,3,0]-non-5-ene (DBN), or1,8-diazabicyclo[5,4,0]-undec-7-ene (DBU).

[0145] Suitable diluents for carrying out the processes (a), (b) and (c)according to the invention are especially inert organic solvents. Theseinclude, in particular, aliphatic, alicyclic or aromatic, optionallyhalogenated hydrocarbons, such as, for example, benzine, benzene,toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether,hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachlorideor 1,4-dichloro-ethane; ethers, such as diethyl ether, diisopropylether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether orethylene glycol diethyl ether; ketones, such as acetone, butanone ormethyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile orbutyronitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone orhexamethylphosphoric triamide; esterssuch as methyl acetate or ethylacetate, sulfoxides, such as dimethyl sulfoxide.

[0146] When carrying out the processes (a), (b) and (c) according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the processes are carried out at temperaturesbetween 0° C. and 150° C., preferably between 10° C. and 120° C.

[0147] The processes (a), (b) and (c) according to the invention aregenerally carried out under atmospheric pressure. However, it is alsopossible to carry out the processes according to the invention underelevated or reduced pressure—in general between 0.1 bar and 10 bar.

[0148] For carrying out the processes (a), (b) and (c) according to theinvention, the starting materials are generally employed inapproximately equimolar amounts. However, it is also possible to use arelatively large excess of one of the components. The reaction isgenerally carried out in a suitable diluent in the presence of adehydrating agent, and the reaction mixture is generally stirred for anumber of hours at the required temperature. Work-up is carried out bycustomary methods (cf. the Preparation Examples).

[0149] The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.By weeds in the broadest sense there are to be understood all plantswhich grow in locations where they are undesired. Whether the substancesaccording to the invention act as total or selective herbicides dependsessentially on the amount used.

[0150] According to the invention, it is possible to treat all plantsand parts of plants. By plants are understood here all plants and plantpopulations such as desired and undesired wild plants or crop plants(including naturally occurring crop plants). Crop plants can be plantswhich can be obtained by conventional breeding and optimization methodsor by biotechnological and genetic engineering methods or combinationsof these methods, including transgenic plants and including plantvarieties which may or may not be protected by plant variety protectionrights. Parts of plants are to be understood as meaning all above-groundand below-ground parts and organs of plants, such as shoot, leaf, flowerand root, examples which may be mentioned being leaves, needles, stems,trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubersand rhizomes. Parts of plants also include crops, and vegetative andgenerative propagation material, for example seedlings, tubers,rhizomes, cuttings and seeds.

[0151] The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by single- ormulti-layer coating.

[0152] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[0153] Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

[0154] Dicotyledonous crops of the genera: Gossypium, Glycine, Beta,Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

[0155] Monocotyledonous weeds of the genera: Echinochloa, Setaria,Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium,Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria,Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum,Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilops,Phalaris.

[0156] Monocotyledonous crops of the genera: Oryza, Zea, Triticum,Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus,Allium.

[0157] However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

[0158] Depending on the concentration, the active compounds according tothe invention are suitable for total weed control, for example onindustrial terrain and rail tracks and on paths and areas with orwithout tree growth. Equally, the active compounds according to theinvention can be employed for controlling weeds in perennial crops, forexample forests, ornamental tree plantings, orchards, vineyards, citrusgroves, nut orchards, banana plantations, coffee plantations, teaplantations, rubber plantations, oil palm plantations, cocoaplantations, soft fruit plantings and hop fields, on lawns and turf andpastures and for selective weed control in annual crops.

[0159] The compounds of the formula (I) according to the invention havestrong herbicidal activity and a broad activity spectrum when applied tothe soil and on above-ground parts of plants. To a certain extent, theyare also suitable for selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops, bothby the pre-emergence and by the post-emergence method.

[0160] The active compounds can be converted into the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusts, pastes, soluble powders, granules,suspoemulsion concentrates, natural and synthetic substances impregnatedwith active compound, and microencapsulations in polymeric substances.

[0161] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is to say liquidsolvents and/or solid carriers, optionally with the use of surfactants,that is to say emulsifiers and/or dispersants and/or foam formers.

[0162] If the extender used is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Liquid solvents whichare mainly suitable are: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol, and also their ethers and esters, ketones, such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulfoxide, and water.

[0163] Suitable solid carriers are: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks, such as calcite, marble, pumice, sepiolite, dolomite andsynthetic granules of inorganic and organic meals, and granules oforganic material, such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates andprotein hydrolyzates; suitable dispersants are: for example lignosulfitewaste liquors and methylcellulose.

[0164] Tackifiers, such as carboxymethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

[0165] It is possible to use colorants, such as inorganic pigments, forexample iron oxide, titanium oxide, Prussian blue, and organic dyes,such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients, such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

[0166] The formulations generally comprise between 0.1 and 95 per centby weight of active compound, preferably between 0.5 and 90%.

[0167] For controlling weeds, the active compounds according to theinvention, as such or in the form of their formulations, can also beused as mixtures with known herbicides, finished formulations or tankmixes being possible.

[0168] Possible components for the mixtures are known herbicides, forexample

[0169] acetochlor, acifluorfen(-sodium), aclonifen, alachlor,alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl),benfuresate, bensulfuron(-methyl), bentazon, benzofenap,benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium),bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate,cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl),chlornitrofen, chlorsulfuron, chlortoluron, cinidon(-ethyl),cinmethylin, cinosulfuron, clethodim, clodinafop(-propargyl), clomazone,clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam(-methyl),cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim,cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate,dicamba, diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid, Auat,dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin,ethametsulfuron(-methyl), ethofumesate, ethoxyfen, ethoxysulfuron,etobenzanid, fenoxaprop(-P-ethyl), flamprop(-isopropyl),flamprop(-isopropyl-L), flamprop(-methyl), flazasulfuron,fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam,flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam,fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam,flupropacil, flurpyrsulfuron(-methyl, -sodium), flurenol(-butyl),fluridone, fluroxypyr(-meptyl), flurprimidol, flurtamone,fluthiacet(-methyl), fluthiamide, fomesafen, glufosinate(-ammonium),glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl),haloxyfop(-P-methyl), hexazinone, imazamethabenz(-methyl),imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr,imazosulfuron, iodosulfuron, ioxynil, isopromilin, isoproturon, isouron,isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactafen, lenacil,linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachlor,methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor,metosulam, metoxuron, metribuzin, metsulfuron(-methyl), molinate,monolinuron, naproanilide, napropamnide, neburon, nicosulfuron,norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,oxaziclomefone, oxyfluorfen, paraquat, pelargonsäure, pendimethalin,pentoxazone, phenmedipham, picolinafen, piperophos, pretilachlor,primmisulfuron(-methyl), prometryn, propachlor, propanil, propaquizafop,propisochlor, propyzamide, prosulfocarb, prosulfuron,pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen,pyribenzoxim, pyributicarb, pyridate, pyriminobac(-methyl),pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine,quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulfuron, sethoxydim,simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl),sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr,tridiphane, trifluralin, triflusulfuron and tritosulfuron.

[0170] A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

[0171] The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing, scattering.

[0172] The active compounds according to the invention can be appliedboth before and after emergence of the plants. They can also beincorporated into the soil before sowing.

[0173] The amount of active compound used can vary within a relativelywide range. It depends essentially on the nature of the desired effect.In general, the amounts used are between 1 g and 10 kg of activecompound per hectare of soil surface, preferably between 5 g and 5 kgper ha.

[0174] The preparation and the use of the active compounds according tothe invention can be seen from the examples below.

PREPARATION EXAMPLES Example 1

[0175]

[0176] At room temperature (about 20° C.), a mixture of 1.64 g (5 mmol)of4-methyl-5-trifluoromethyl-2-(3-chloro-4-carboxy-phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,0.62 g (5.5 mmol) of 1-ethyl-5-hydroxy-pyrazole and 40 ml ofacetonitrile is admixed with stirring with 1.13 g (5.5 mmol) ofdicyclohexylcarbodiimide, and the reaction mixture is stirred at roomtemperature for 16 hours. 1.0 g (10 mmol) of triethylamine and 0.2 g (2mmol) of trimethylsilyl cyanide are then added, and the mixture isstirred at room temperature for three days. 60 ml of a 2% strengthaqueous sodium carbonate solution are then added and the mixture isstirred at room temperature for three hours. The precipitateddicyclohexylurea is removed by filtration with suction, and the motherliquor is extracted twice with diethyl ether. With stirring, the aqueousphase is adjusted by addition of conc. hydrochloric acid to a pH ofabout 1. The oily product that separates off during the addition isextracted with methylene chloride, and the extraction solution is driedwith magnesium sulfate and filtered. From the filtrate, the solvent iscarefully distilled off under waterpump vacuum.

[0177] This gives 1.5 g (72% of theory) of4-methyl-5-trifluoromethyl-2-[3-chloro-4-(1-ethyl-5-hydroxy-pyrazol-4-yl-carbonyl)-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one as anamorphous product.

[0178] logP (determined at pH=2): 2.63.

[0179] Similarly to Example 1, and in accordance with the generaldescription of the preparation process according to the invention, it isalso possible to prepare, for example, the compounds of the generalformula (I)—or those of the formulae (IA), (IB) or (IC)—listed in Table1 below. TABLE 1 Examples of the compounds of the formula (I), (IA),(IB), (IC) Here, Y in each-case represents hydrogen

(IA)

(IB)

(IC) Ex. (Position) (Formula) No. A Q R¹ R² R³ (R⁴)_(n) R⁵ R⁶ Physicaldata 2 CH₂ O C₂H₅ H CF₃ — OC₂H₅ CH₃ (IA) logP = 2.34^(a)) 3 CH₂ O C₂H₅ HCF₃ — SCH₃ CH₃ (IA) logP = 2.22 ^(a)) 4 CH₂ O C₂H₅ H SO₂CH₃ — SCH₃ CH₃(IA) logP = 1.24^(a)) 5 CH₂ O C₂H₅ H CF₃ — SC₂H₅ CH₃ (IA) logP =2.58^(a)) 6 CH₂ O C₂H₅ H CF₃ — SC₃H₇i CH₃ (IA) logP =2.90^(a)) 7 CH₂ OC₂H₅ H CF₃ — OCH₃

(IA) logP = 2.28^(a)) 8 CH₂ O C₂H₅ H F — N(CH₃)₂ CH₃ (IA) logP=1.61^(a)) 9 CH₂ O CH₃ CH₃ F — N(CH₃)₂ CH₃ (IA) logP =1.32^(a)) 10 CH₂ OCH₃ CH₃ F — OCH₃

(IA) logP = 1.50^(a)) 11 CH₂ O CH₃ CH₃ F — OC₂H₅

(IA) logP = 1.80^(a)) 12 CH₂ O C₂H₅ H Br —

CH₃ (IA) logP = 2.69^(a)) 13 — O C₂H₅ H H (6-) CF₃ CF₃ CH₃ (IB) logP =2.83^(a)) 14 — O C₂H₅ H H (2-) Cl CH₃ CH₃ (IC) logP =1.71^(a)) 15 — OC₂H₅ H H — CF₃ CH₃ (IA) logP =1.95^(a)) 16 — O C₂H₅ H Cl — CF₃ CH₃ (IA)logP = 2.47^(a)) 17 CH₂ O C₂H₅ H Cl (2-) Cl CF₃ CH₃ (IB) logP =2.30^(a)) 18 CH₂ O C₂H₅ H Cl (2-) Cl SCH₃ CH₃ (IB) logP = 1.91^(a)) 19CH₂ O C₂H₅ H Cl (2-) Cl OC₂H₅ CH₃ (IB) logP = 2.01^(a)) 20 CH₂ O C₂H₅ HCl (2-) Cl

(IB) logP = 2.14^(a)) 21 CH₂ O C₂H₅ H CI (2-) Cl OCH₃ CH₃ (IB) logP =1.69^(a)) 22 CH₂ O C₂H₅ H Cl (2-) Cl OC₃H₇-i CH₃ (IB) logP = 2.31^(a))23 CH₂ O C₂H₅ H Cl (2-) Cl OCH₂CF₃ CH₃ (IB) logP = 2.33^(a)) 24 CH₂ OC₂H₅ H Cl (2-) Cl Br CH₃ (IB) logP = 1.81^(a)) 25 CH₂ O C₂H₅ H Cl (2-)Cl H CH₃ (IB) logP = 1.28^(a)) 26 CH₂ O C₂H₅ H Cl (2-) Cl

CH₃ (IB) logP = 1.82^(a)) 27 — O C₂H₅ H Br — CF₃ CH₃ (IA) logP =2.55^(a)) 28 CH₂ O C₂H₅ H Cl (2-) Cl N(CH₃)₂ CH₃ (IB) logP = 1.77^(a))29 CH₂ O C₂H₅ H Cl (2-) Cl CH₃ CH₃ (IB) logP = 1.38^(a)) 30 CH₂ O C₂H₅ HCl (2-) Cl R⁵ + R⁶: (cF. R⁵) (IB) (CH₂)₄ logP = 1.55^(a)) 31 CH₂ O C₂H₅H Cl (2-) Cl OCH₃

(IB) logP = 1.99^(a)) 32 CH₂ O C₂H₅ H Cl (2-) Cl OC₂H₅

(IB) logP = 2.31^(a)) 33 CH₂ O C₂H₅ H Cl (2-) Cl OC₃H₇-i

(IB) logP = 4.64^(a)) 34 CH₂ O C₂H₅ H Cl (2-) Cl OCH₂CF₃

(IB) logP = 2.65^(a)) 35 CH₂ O C₂H₅ H Cl (2-) Cl SCH₃

(IB) logP = 2.27^(a)) 36 CH₂ O C₂H₅ H Cl (2-) Cl CH₃

(IB) logP = 1.64^(a)) 37 CH₂ O C₂H₅ H Cl (2-) Cl N(CH₃)₂

(IB) logP = 2.04^(a)) 38 CH₂ O C₂H₅ H Cl (2-) Cl C₂H₅ OC₂H₅ (IB) logP =2.16^(a)) 39 CH₂ O CH₃ CH₃ Cl (2-) Cl Br CH₃ (IB) logP = 1.52^(a)) 40CH₂ O CH₃ H Cl (2-) Cl Br CH₃ (IB) logP = 1.53^(a)) 41 CH₂ O C₂H₅ CH₃ Cl(2-) Cl SCH₃ CH₃ (IB) logP = 1.91^(a)) 42 CH₂ O C₂H₅ CH₃ Cl (2-) ClOC₂H₅ CH₃ (IB) logP = 2.02^(a)) 43 CH₂ O C₂H₅ CH₃ Cl (2-) Cl OCH₃ CH₃(IB) logP = 1.71^(a)) 44 CH₂ O C₂H₅ CH₃ Cl (2-) Cl Br CH₃ (IB) logP =1.81^(a)) 45 CH₂ O C₂H₅ CH₃ Cl (2-) Cl CH₃ CH₃ (IB) logP = 1.40^(a)) 46CH₂ O t-C₄H₉ CH₃ Cl (2-) Cl SCH₃ CH₃ (IB) logP = 3.30^(a)) 47 CH₂ Ot-C₄H₉ CH₃ Cl (2-) Cl OC₂H₅ CH₃ (IB) logP = 3.44^(a)) 48 CH₂ O t-C₄H₉CH₃ Cl (2-) Cl OCH₃ CH₃ (IB) logP = 3.02^(a)) 49 CH₂ O t-C₄H₉ CH₃ Cl(2-) Cl Br CH₃ (IB) logP = 3.19^(a)) 50 CH₂ O t-C₄H₉ CH₃ Cl (2-) Cl CH₃CH₃ (IB) logP = 2.53^(a)) 51 CH₂ O CH₃ CH₃ Cl (2-) Cl SCH₃ CH₃ (IB) logP= 1.66^(a)) 52 CH₂ O CH₃ CH₃ Cl (2-) Cl OC₂H₅ CH₃ (IB) logP = 1.76^(a))53 CH₂ O CH₃ CH₃ Cl (2-) Cl OCH₃ CH₃ (IB) logP = 1.48^(a)) 54 CH₂ O CH₃CH₃ Cl (2-) Cl CH₃ CH₃ (IB) logP = 1.20^(a)) 55 CH₂ O CH₃ H Cl (2-) ClSCH₃ CH₃ (IB) logP =1.67^(a)) 56 CH₂ O CH₃ H Cl (2-) Cl OC₂H₅ CH₃ (IB)logP =1.77^(a)) 57 CH₂ O CH₃ H Cl (2-) Cl OCH₃ CH₃ (IB) logP =1.48^(a))58 CH₂ O CH₃ H Cl (2-) Cl CH₃ CH₃ (IB) logP = 1.19^(a)) 59 CH₂ O C₂H₅ HOCH₃ (2-) OC₂H₅ CH₃ (IC) NO₂ logP = 1.99^(a)) 60 CH₂ O C₂H₅ H OCH₃ (2-)SCH₃ CH₃ (IC) NO₂ logP = 1.92^(a)) 61 CH₂ O C₂H₅ H CF₃ — SCH₃ CH₃ (IA-Nasalt) 62 CH₂ O C₂H₅ H Cl (2-) F SCH₃ CH₃ (IB) logP = 1.99^(a)) 63 CH₂ OC₂H₅ H CF₃ — H CH₃ (IA) 64 CH₂ O C₂H₅ H CF₃ — CH₃ CH₃ (IA) logP =1.80^(a)) 65 CH₂ O C₂H₅ H CF₃ — CH₂OCH₃ CH₃ (IA) logP = 1.98^(a)) 66 CH₂O C₂H₅ H CF₃ — OCH₃ CH₃ (IA) logP = 2.27^(a)) 67 CH₂ O C₂H₅ H SO₂CH₃ —CF₃ CH₃ (IA) logP = 1.60^(a)) 68 CH₂ O C₂H₅ H SO₂CH₃ — OCH₂CF₃ CH₃ (IA)logP = 1.73^(a)) 69 CH₂ O C₂H₅ H F (2-) Cl CH₃ CH₃ (IB) logP = 1.27^(a))70 CH₂ O C₂H₅ H F (2-) Cl SCH₃ CH₃ (IB) logP = 1.76^(a)) 71 CH₂ O C₂H₅ HF (2-) Cl OCH₃ CH₃ (IB) logP = 1.55^(a)) 72 CH₂ O C₂H₅ H F (2-) ClN(CH₃)₂ CH₃ (IB) logP = 1.62^(a)) 73 CH₂ O C₂H₅ H SO₂CH₃ (2-) Cl SCH₃CH₃ (IB) m.p.: 204° C. 74 CH₂ O C₂H₅ H SO₂CH₃ (2-) Cl OCH₃ CH₃ (IB)m.p.: 183° C. 75 CH₂ O C₂H₅ H SO₂CH₃ (2-) Cl OCH₂CF₃ CH₃ (IB) m.p.: 192°C. 76 CH₂ O C₂H₅ H SO₂CH₃ (2-) Cl CH₃ CH₃ (IB) m.p.: 200° C. 77 CH₂ OC₂H₅ H SO₂CH₃ (2-) Cl OCH₃

(IB) m.p.: 205° C. 78 CH₂ O C₂H₅ H SO₂CH₃ (2-) Cl SCH₃

(IB) m.p.: 233° C. 79 CH₂ O C₂H₅ H SO₂CH₃ (2-) Cl CH₃

(IB) m.p.: 223° C. 80 CH₂ O C₂H₅ H SO₂CH₃ (2-) Cl C₂H₅ OC₂H₅ (IB) m.p.:163° C.

[0180] Similarly to Example 1, and in accordance with the generaldescription of the preparation process according to the invention, it isalso possible to prepare, for example, the compounds of the generalformula (I)—or of the formula (ID)—listed in Table 2 below. TABLE 2Further examples of the compounds of the formula (I)

(ID) Ex. (Position) (Position) (Position) No. R¹ R² R³ (R⁴)_(n) —A—Z YPhysical data ID-1 C₂H₅ H (2-) Cl (4-) Cl

H logP = 1.64^(a)) ID-2 C₂H₅ H (2-) Cl (4-) Cl

H logP = 1.77^(a)) ID-3 CH₃ H (2-) Cl (4-) Cl

H logP = 1.52^(a)) ID-4 CH₃ CH₃ (2-) Cl (4-) Cl

H logP = 1.50^(a)) ID-5 C₂H₅ CH₃ (2-) Cl (4-) Cl

H logP = 1.72^(a)) ID-6 t-C₄H₉ CH₃ (2-) Cl (4-) Cl

H logP = 3.01^(a)) ID-7 C₂H₅ H (4-) CF₃ —

H logP = 2.98^(a)) ID-8 C₂H₅ H (4-) CF₃ —

H logP = 2.75^(a)) ID-9 C₂H₅ H (4-) CF₃ —

logP = 3.82^(a)) ID-10 C₂H₅ H (4-) CF₃ —

logP = 3.73^(a)) ID-11 C₂H₅ H (4-) CF₃ —

logP = 3.25^(a)) ID-12 C₂H₅ H (4) CF₃ —

logP = 2.82^(a)) ID-13 C₂H₅ H (4-) CF₃ —

CH₃ logP = 2.74^(a)) ID-14 C₂H₅ H (4-) CF₃ —

C₂H₅ logP = 2.82^(a)) ID-15 C₂H₅ H (4-) CF₃ —

i-C₃H₇ logP = 3.11^(a)) ID-16 C₂H₅ H (4-) CF₃ —

logP = 2.99^(a)) ID-17 C₂H₅ H (4-) CF₃ —

logP = 3.45^(a)) ID-18 C₂H₅ H (4-) CF₃ —

logP = 3.79^(a)) ID-19 C₂H₅ H (4-) CF₃ —

logP = 3.97^(a)) ID-20 C₂H₅ H (4-) CF₃ —

logP = 3.12^(a)) ID-21 C₂H₅ H (4-) CF₃ —

logP = 3.49^(a)) ID-22 C₂H₅ H (4-) CF₃ —

logP = 3.85^(a)) ID-23 C₂H₅ H (4-) CF₃ —

logP = 4.26^(a)) ID-24 C₂H₅ H (4-) CF₃ —

logP = 3.84^(a)) ID-25 C₂H₅ H (4-) CF₃ —

logP = 3.33^(a)) ID-26 C₂H₅ H (4-) CF₃ —

logP = 3.98^(a)) ID-27 C₂H₅ H (4-) CF₃ —

logP = 3.94^(a)) ID-28 C₂H₅ H (4-) CF₃ —

logP = 3.57^(a)) ID-29 C₂H₅ H (4-) CF₃ —

logP = 3.75^(a)) ID-30 C₂H₅ H (4-) CF₃ —

CH₃ logP = 2.65^(a)) ID-31 C₂H₅ H (4-) CF₃ —

C₂H₅ logP = 2.71^(a)) ID-32 C₂H₅ H (4-) CF₃ —

i-C₃H₇ logP = 3.00^(a)) ID-33 C₂H₅ H (4-) CF₃ —

logP = 2.89^(a)) ID-34 C₂H₅ H (4-) CF₃ —

logP = 3.37^(a)) ID-35 C₂H₅ H (4-) CF₃ —

logP = 3.71^(a)) ID-36 C₂H₅ H (4-) CF₃ —

logP = 3.89^(a)) ID-37 C₂H₅ H (4-) CF₃ —

logP = 3.06^(a)) ID-38 C₂H₅ H (4-) CF₃ —

logP = 3.41^(a)) ID-39 C₂H₅ H (4-) CF₃ —

logP = 3.78^(a)) ID-40 C₂H₅ H (4) CF₃ —

logP = 4.17^(a)) ID-41 C₂H₅ H (4-) CF₃ —

logP = 3.76^(a)) ID-42 C₂H₅ H (4-) CF₃ —

logP = 3.26^(a)) ID-43 C₂H₅ H (4-) CF₃ —

logP = 3.89^(a)) ID-44 C₂H₅ H (4-) CF₃ —

logP = 3.85^(a)) ID-45 C₂H₅ H (4-) CF₃ —

logP = 3.19^(a)) ID-46 C₂H₅ H (4-) CF₃ —

logP = 3.47^(a)) ID-47 C₂H₅ H (4-) CF —

logP = 3.64^(a)) ID-48 C₂H₅ H (2-) OCH₃ (4-) Cl

H ID-49 C₂H₅ H (2-) OCH₃ (4-) Cl

H ID-50 CH₃ H (2-) Cl (4-) Cl

H logP = 1.41^(a)) ID-51 CH₃ CH₃ (2-) Cl (4-) Cl

H logP = 1.38^(a)) ID-52 C₂H₅ CH₃ (2-) Cl (4-) Cl

H logP = 1.56^(a)) ID-53 t-C₄H₉ CH₃ (2-) Cl (4-) Cl

H logP = 2.79^(a)) ID-54 CH₃ H (2-) Cl (4-) Cl

H logP = =1.62^(a)) ID-55 CH₃ CH₃ (2-) Cl (4-) Cl

H logP = 1.57^(a)) ID-56 C₂H₅ H (2-) Cl (4-) Cl

H logP = 1.88^(a)) ID-57 C₂H₅ CH₃ (2-) Cl (4-) Cl

H logP = 1.79^(a)) ID-58 t-C₄H₉ CH₃ (2-)Cl (4-)Cl

H logP = 3.15^(a))

[0181] The logP values given in Tables 1 and 2 were determined inaccordance with EEC Directive 79/831 Annex V.A8 by HPLC (HighPerformance Liquid Chromatography) on a reversed-phase column (C 18).Temperature: 43° C.

[0182] (a) Mobile phases for the determination in the acidic range: 0.1%aqueous phosphoric acid, acetonitrile; linear gradient from 10%acetonitrile to 90% acetonitrile—corresponding measurement results inTable 1 are marked ^(a)).

[0183] (b) Mobile phases for the determination in the neutral range:0.01 molar aqueous phosphate buffer solution, acetonitrile; lineargradient from 10% acetonitrile to 90% acetonitrile—correspondingmeasurement results in Table 1 are marked ^(b)).

[0184] Calibration was carried out using unbranched alkan-2-ones (having3 to 16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones).

[0185] The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

Starting Materials of Formula (III): Example (III-1)

[0186]

[0187] 4.5 g (15 mmol) of2-(3-chloro-4-cyano-phenyl)-4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-oneare taken up in 80 ml of 60% strength sulfuric acid, and the mixture isheated at reflux for 6 hours. After cooling to room temperature, theresulting crystalline product is isolated by filtration with suction.

[0188] This gives 4.5 g (91% of theory) of2-(3-carboxy-4-chloro-phenyl)-4-methyl-5-trifluoromethyl-2,4-dihydro-3H-2,4-triazol-3-oneof melting point 223° C.

Example (III-2)

[0189]

[0190] 2 g (4.9 mmol) of5-bromo-4-methyl-2-(2-ethoxycarbonyl-5-trifluoromethyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one(cf. Example IV-1) are dissolved in 30 ml of 10% strength ethanolicpotassium hydroxide solution and heated at reflux for 2 hours. Thereaction mixture is concentrated under waterpump vacuum and the residueis taken up in 20 ml of water and acidified with dilute hydrochloricacid. The precipitated solid is filtered and dried.

[0191] This gives 1.2 g (71% of theory) of5-ethoxy4-methyl-2-(2-carboxy-5-trifluoromethyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneas a solid product.

[0192] logP: 2.18^(a))

Example (III-3)

[0193]

[0194] 13.4 g (35 mmol) of4-methyl-5-trifluoromethyl-2-(2,6-dichloro-3-methoxycarbonyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneare initially charged in 60 ml of 1,4-dioxane, and a solution of 1.54 g(38.5 mmol) of sodium hydroxide in 20 ml of water is slowly metered inat room temperature. The reaction mixture is stirred at 60° C. for 150minutes and then concentrated under waterpump vacuum. The residue isdissolved in 100 ml of water, and the pH of the solution is adjusted to1 by addition of conc. hydrochloric acid. The resulting crystallineproduct is isolated by filtration with suction.

[0195] This gives 11.7 g (90% of theory) of4-methyl-5-trifluoromethyl-2-(2,6-dichloro-3-carboxy-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 207° C.

[0196] Similarly to Examples (III-1) to (III-3), it is also possible toprepare, for example, the compounds of the general formula (III) listedin Table 3 below. TABLE 32 Examples of the compounds of the formula(III)

(III) (Position) (Position) (Position) Ex. No R³ (R⁴)_(n) —A—Z Physicaldata III-4 (4-) Cl —

logP = 1.39^(a)) III-5 (4-) SO₂CH₃ —

logP = 1.47^(a)) III-6 (4-) F —

logP = 1.73^(a)) III-7 (4-) CF₃ —

logP = 1.65^(a)) III-8 (4-) Br —

logP = 1.74^(a)) III-9 (4-) CF₃ —

logP = 2.43^(a)) III-10 (4-) CF₃ —

logP = 2.12^(a)) III-11 (4-) CF₃ —

logP= 1.61^(a)) III-12 (4-) CF₃ —

logP = 1.93^(a)) III-13 (4-) CF₃ —

logP = 2.01^(a)) III-14 (4-) CF₃ —

logP = 1.77^(a)) III-15 (3-) CH₃ —

logP = 1.70^(a)) III-16 (4-) SO₂CH₃ —

logP = 1.07^(a)) III-17 (4-) CF₃ —

logP = 2.35^(a)) III-18 (4-) CF₃ —

logP = 2.63^(a)) III-19 (4-) CF₃ —

logP = 2.13^(a)) III-20 (4-) CF₃ —

logP = 1.82^(a)) III-21 (4-) CF₃ —

logP = 2.48^(a)) III-22 (4-) CF₃ —

logP = 1.73^(a)) III-23 (4-) CF₃ —

logP = 3.11^(a)) III-24 (4-) F —

logP = 1.43^(a)) III-25 (4-) F —

logP = 1.97^(a)) III-26 (4-) F —

logP = 1.30^(a)) III-27 (4-) F —

logP = 1.63^(a)) III-28 (4-) F —

logP = 1.93^(a)) III-29 (4-) CF₃ —

logP = 1.78^(a)) III-30 (2-) Cl (4-) Cl

m.p.: 230° C. logP = 1.63^(a)) III-31 (2-) Cl (4-) Cl

m.p.: 190° C. logP = 1.73^(a)) III-32 (2-) Cl (4-) Cl

m.p.: 210° C. logP = 1.87^(a)) III-33 (2-) Cl (4-) Cl

m.p.: 210° C. logP = 1.43^(a)) III-34 (2-) Cl (4-) Cl

m.p.: 164° C. logP = 2.01^(a)) III-35 (2-) Cl (4-) Cl

m.p.: 168° C. logP = 2.04^(a)) III-36 (2-) Cl (4-) Cl

m.p.: 218° C. logP = 1.53^(a)) III-37 (2-) Cl (4-) Cl

m.p.: 259° C. logP = 0.98^(a)) III-38 (2-) Cl (4-) Cl

m.p.: 210° C. logP = 1.56^(a)) III-39 (2-) Cl (4-) Cl

m.p.: 197° C. logP = 1.51^(a)) III-40 (2-) Cl (4-) Cl

m.p.: 262° C. logP = 1.11^(a)) III-41 (2-) Cl (4-) Cl

m.p.: 249° C. logP = 1.30^(a)) III-42 (2-) Cl (4-) Cl

m.p.: 200° C. logP = 1.71^(a)) III-43 (2-) Cl (4-) Cl

m.p.: 189° C. logP = 2.01^(a)) III-44 (2-) Cl (4-) Cl

m.p.: 178° C. logP = 2.28^(a)) III-45 (2-) Cl (4-) Cl

m.p.: 161° C. logP = 2.31^(a)) III-46 (2-) Cl (4-) Cl

m.p.: 200° C. logP = 1.98^(a)) III-47 (2-) Cl (4-) Cl

m.p.: 201° C. logP = 1.39^(a)) III-48 (2-) Cl (4-) Cl

m.p.: 207° C. logP = 1.77^(a)) III-49 (2-) Cl (4-) Cl

m.p.: 140° C. logP = 1.88^(a)) III-50 (4-) OCH₂CHF₂ —

m.p.: 154° C. logP = 2.14^(a)) III-51 — —

m.p.: 214° C. logP = 1.87^(a)) III-52 — —

m.p.: 194° C. logP = 2.07^(a)) III-53 — —

m.p.: 181° C. logP = 1.97^(a)) III-54 — —

m.p.: 251° C. logP = 1.14^(a)) III-55 (2-) Cl (4-) Cl

logP = 1.38^(a)) III-56 (2-) Cl (4-) Cl

logP = 1.48^(a)) III-57 (2-) Cl (4-) Cl

III-58 (4-) Cl —

¹H-NMR (DMSO-D6, δ): 5.42 ppm. III-59 (4-) CF₃ —

¹H-NMR (DMSO-D6, δ): 5.48 ppm. III-60 (4-) CF₃ —

¹H-NMR (DMSO-D6, δ): 5.60 ppm. logP = 2.47^(a)) III-61 (4-) CF₃ —

logP = 2.33^(a)) III-62 (4-) SO₂CH₃ —

¹H-NMR (DMSO-D6, δ): 5.14 ppm. III-63 (4-) SO₂CH₃ —

¹H-NMR (DMSO-D6, δ): 5.27 ppm. III-64 (4-) Cl —

¹H-NMR (CDCl₃, δ): 5.12 ppm. III-65 (4-) Cl —

¹H-NMR (DMSO-D6, δ): 5.20 ppm. III-66 (4-) Cl —

¹H-NMR (DMSO-D6, δ): 5.03 ppm. III-67 (4-) Br —

¹H-NMR (DMSO-D6, δ): 5.24 ppm. III-68 (4-) Br —

¹H-NMR (DMSO-D6, δ): 5.39 ppm. III-69 (4-) F —

¹H-NMR (DMSO-D6, δ): 5.19 ppm. III-70 (4-) F —

¹H-NMR (DMSO-D6, δ): 5.30 ppm. III-71 (4-) F —

¹H-NMR (DMSO-D6, δ): 5.43 ppm. III-72 (4-) Br —

¹H-NMR (DMSO-D6, δ): 5.10 ppm. III-73 (4-) Br —

¹H-NMR (DMSO-D6, δ): 5.03 ppm. III-74 (4-) Br —

¹H-NMR (DMSO-D6, δ): 5.19 ppm. III-75 (4-) Br —

¹H-NMR (DMSO-D6, δ): 5.01 ppm. III-76 (4-) Cl —

¹H-NMR (DMSO-D6, δ): 5.14 ppm. III-77 (4-) Cl —

¹H-NMR (DMSO-D6, δ): 5.25 ppm. III-78 (4-) NO₂ —

¹H-NMR (DMSO-D6, δ): 5.23 ppm. III-79 (4-) NO₂ —

¹H-NMR (DMSO-D6, δ): 5.37 ppm. III-80 (4-) CF₃ —

logP = 2.46^(a)) III-81 (4-) CF₃ —

¹H-NMR (DMSO-D6, δ): 5.31 ppm. III-82 (4-) CF₃ —

logP = 2.08^(a)) III-83 (4-) OCH₃ —

¹H-NMR (CDCl₃, δ): 5.38 ppm. III-84 (4-) OCH₃ —

¹H-NMR (CDCl₃, δ): 5.43 ppm. III-85 (4-) CF₃ —

¹H-NMR (CDCl₃, δ): 5.47 ppm. III-86 (4-) Br —

logP = 1.44^(a)) III-87 (4-) Br —

logP = 1.63^(a)) III-88 (4-) Br —

logP = 2.27^(a)) III-89 (4-) Br —

logP = 2.31^(a)) III-90 — —

logP = 1.82^(a)) III-91 (4-) Br —

¹H-NMR (CDCl₃, δ): 5.32 ppm. III-92 (4-) Br —

¹H-NMR (CDCl₃, δ): 5.53 ppm. III-93 (4-) F —

¹H-NMR (CDCl₃, δ): 5.39 ppm. III-94 (4-) F —

¹H-NMR (CDCl₃, δ): 5.57 ppm. III-95 (4-) F —

¹H-NMR (CDCl₃, δ): 5.44 ppm. III-96 (4-) F —

¹H-NMR (CDCl₃, δ): 5.41 ppm. III-97 — —

¹H-NMR (CDCl₃, δ): 5.34 ppm. III-98 — —

¹H-NMR (CDCl₃, δ): 5.38 ppm. III-99 — —

¹H-NMR (CDCl₃, δ): 5.26 ppm. III-100 — —

¹H-NMR (CDCl₃, δ): 5.43 ppm. III-101 — —

logP= 1.23^(a)) III-102 (4-) SO₂CH₃ —

logP = 1.14^(a)) III-103 (4-) CF₃ —

logP = 2.45^(a)) III-104 (4-) CF₃ —

logP = 2.48^(a)) III-105 (4-) Br — (2-)

logP = 1.85^(a)) III-106 (4-) CF₃ —

logP = 2.74^(a)) III-107 (4-) CF₃ —

logP = 2.01^(a)) III-108 (4-) CF₃ —

logP = 1.79^(a)) III-109 (4-) CF₃ —

logP = 1.65^(a)) III-110 (4-)Br —

logP= 1.90^(a)) III-111 (4-) Cl —

logP = 1.83^(a)) III-112 (4-) I —

logP = 2.06^(a)) III-113 (4-) I —

m.p.: 104° C. logP = 2.39^(a)) III-114 (4-) Br —

m.p.: 191° C. III-115 (4-) Br —

m.p.: 213° C. III-116 — —

III-117 — —

m.p.: 112° C. III-118 (4-)CF₃ —

m.p.: 158° C. III-119 (4-) CF₃ —

m.p.: 162° C. III-120 (4-) Cl (5-) Cl

m.p.: 167° C. III-121 — —

m.p.: 188° C. III-122 — —

III-123 — —

m.p.: 131° C. III-124 (4-) Cl —

m.p.: 109° C. III-125 (4-) I —

m.p.: 104° C. III-126 (4-) Br —

m.p.: 99° C. III-127 (4-) Br —

m.p.: 174° C. III-128 — —

m.p.: 122° C. III-129 (4-) Br —

m.p.: 164° C. III-130 — —

m.p.: 154° C. III-131 (4-)Br —

m.p.: 161° C. III-132 (4-) CN —

m.p.: 196° C. III-133 — —

m.p.: 192° C. III-134 — —

[0197] The logP values given in Table 3 were determined in accordancewith EEC Directive 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) on a reversed-phase column (C 18). Temperature: 43° C.

[0198] (a) Mobile phases for the determination in the acidic range: 0.1%aqueous phosphoric acid, acetonitrile; linear gradient from 10%acetonitrile to 90% acetonitrile—corresponding measurement results inTable 1 are marked ^(a)).

[0199] (b) Mobile phases for the determination in the neutral range:0.01 molar aqueous phosphate buffer solution, acetonitrile; lineargradient from 10% acetonitrile to 90% acetonitrile—correspondingmeasurement results in Table 1 are marked ^(b)).

[0200] Calibration was carried out using unbranched alkan-2-ones (having3 to 16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones).

[0201] The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

Starting Materials of the Formula (IV) Example (IV-1)

[0202]

[0203] Step 1

[0204] 10 g (49 mmol) of 2-methyl-4-trifluoromethyl-benzoic acid aredissolved in 150 ml of ethanol and admixed with 1 ml of conc. sulfuricacid. The solution is heated at reflux for 24 hours and thenconcentrated, the residue is taken up in methylene chloride and themixture is extracted with aqueous sodium bicarbonate solution. Themethylene chloride phase is dried over sodium sulfate and concentratedunder waterpump vacuum.

[0205] This gives 9 g (80% of theory) of ethyl2-methyl-4-trifluoromethyl-benzoate as an amorphous residue.

[0206] Step 2

[0207] 9 g (39 mmol) of ethyl 2-methyl-4-trifluoromethyl-benzoate aredissolved in 200 ml of carbon tetrachloride and admixed with 7 g (39mmol) of N-bromo-succinimide and 0.1 g of dibenzoyl peroxide. Themixture is heated at reflux for 6 hours, and the precipitatedsuccinimide is then filtered and the filtrate is concentrated underwaterpump vacuum.

[0208] This gives 12 g of an amorphous residue which, in addition toethyl 2-bromomethyl-4-trifluoromethyl-benzoate, also contains 17% ofethyl 2,2-dibromomethyl-4-trifluoromethyl-benzoate and 12% of ethyl2-methyl-4-trifluoromethyl-benzoate.

[0209] Step 3

[0210] 4 g of ethyl 2-bromomethyl-4-trifluoromethyl-benzoate (about 70%pure) and 2.28 g (12.8 mmol) of5-bromo-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 150ml of acetonitrile, admixed with 5.3 g (38.4 mmol) of potassiumcarbonate and, with vigorous stirring, heated at reflux for 2 hours. Thereaction mixture is taken up in water and extracted repeatedly withmethylene chloride. The combined methylene chloride phases are driedover sodium sulfate, concentrated under waterpump vacuum andchromatographed.

[0211] This gives 2 g (38% of theory) of5-bromo-4-methyl-2-(2-ethoxycarbonyl-5-trifluoromethyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneas an amorphous product.

[0212]¹H-NMR (CDCl₃, δ): 5.46 ppm.

Example (IV-2)

[0213]

[0214] 6.7 g (40 mmol) of4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one areinitially charged in 150 ml of acetonitrile and stirred with 11 g (80mmol) of potassium carbonate. The mixture is heated to 50° C., and asolution of 13.1 g (44 mmol) of methyl3-bromomethyl-2,4-dichloro-benzoate in 20 ml of acetonitrile is thenadded dropwise with stirring, and the reaction mixture is heated atreflux with stirring for 15 hours. The mixture is then concentratedunder waterpump vacuum and the residue is taken up in methylenechloride, washed with 1N hydrochloric acid, dried with sodium sulfateand filtered. The filtrate is concentrated under reduced pressure, theresidue is digested with petroleum ether and the resulting crystallineproduct is isolated by filtration with suction.

[0215] This gives 14.9 g (97% of theory) of4-methyl-5-trifluoromethyl-2-(2,6-dichloro-3-methoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 109° C.

[0216] Similarly to Examples (IV-1) and (IV-2), it is also possible toprepare, for example, the compounds of the general formula (IV) listedin Table 4 below. TABLE 4 (IV)

Examples of the compounds of the formula (IV) (Position) (Position)(Position) Physical Ex. No. R³ (R⁴)_(n) —A—Z X data IV-3 (2-) Cl (4-) Cl

OCH₃ m.p.: 229° C. logP = 2.27^(a)) IV-4 (2-) Cl (4-) Cl

OCH₃ m.p.: 120° C. logP = 2.38^(a)) IV-5 (2-) Cl (4-) Cl

OCH₃ m.p.: 127° C. logP = 2.55^(a)) IV-6 (2-) Cl (4-) Cl

OCH₃ m.p.: 121° C. logP = 2.04^(a)) IV-7 (2-) Cl (4-) Cl

OCH₃ m.p.: 68° C. logP = 2.73^(a)) IV-8 (2-) Cl (4-) Cl

OCH₃ m.p.: 129° C. logP = 2.72^(a)) IV-9 (2-) Cl (4-) Cl

OCH₃ m.p.: 164° C. logP = 2.18^(a)) IV-10 (2-) Cl (4-) Cl

OCH₃ m.p.: 158° C. logP = 1.55^(a)) IV-11 (2-) Cl (4-) Cl

OCH₃ m.p.: 106° C. logP = 2.16^(a)) IV-12 (2-) Cl (4-) Cl

OCH₃ m.p.: 126° C. logP = 2.11^(a)) IV-13 (2-) Cl (4-) Cl

OCH₃ m.p.: 146° C. logP = 1.65^(a)) IV-14 (2-) Cl (4-) Cl

OCH₃ m.p.: 178° C. logP = 1.86^(a)) IV-15 (2-) Cl (4-) Cl

OCH₃ m.p.: 97° C. logP = 2.36^(a)) IV-16 (2-) Cl (4-) Cl

OCH₃ m.p.: 99° C. logP = 2.73^(a)) IV-17 (2-) Cl (4-) Cl

OCH₃ m.p.: 56° C. logP = 2.27^(a)) IV-18 (2-) Cl (4-) Cl

OCH₃ m.p.: 102° C. logP = 3.05^(a)) IV-19 (2-) Cl (4-) Cl

OCH₃ m.p.: 131° C. logP = 2.70^(a)) IV-20 (2-) Cl (4-) Cl

OCH₃ m.p.: 135° C. logP = 1.97^(a)) IV-21 (2-) Cl (4-) Cl

OCH₃ m.p.: 143° C. logP = 2.42^(a)) IV-22 (2-) Cl (4-) Cl

OCH₃ m.p.: 85° C. logP = 2.58^(a)) IV-23 (2-) Cl (4-) Cl

OCH₃ logP = 1.98^(a)) IV-24 (2-) Cl (4-) Cl

OCH₃ logP = 2.07^(a)) IV-25 (2-) Cl (4-) Cl

OCH₃ m.p.: 157° C. logP = 2.94^(a)) IV-26 (4-) CF₃ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.53 ppm. IV-27 (4-) NO₂ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.48 ppm. IV-28 (4-) NO₂ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.30 ppm. IV-29 (4-) SO₂CH₃ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.61 ppm. IV-30 (4-) Cl —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.08 ppm. IV-31 (4-) Cl —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.17 ppm. IV-32 (4-) Cl —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.00 ppm. IV-33 (4-) SO₂CH₃ —

OC₂H₅ logP = 1.53^(a)) IV-34 (4-) Br —

OC₂H₅ logP = 3.24^(a)) IV-35 (4-) Br —

OC₂H₅ logP = 3.40^(a)) IV-36 (4-) F —

OC₂H₅ logP = 2.41^(a)) IV-37 (4-) F —

OC₂H₅ logP = 2.45^(a)) IV-38 (4-) Br —

OC₂H₅ logP = 2.06^(a)) IV-39 (4-) Br —

OC₂H₅ logP = 2.64^(a)) IV-40 (4-) Br —

OC₂H₅ logP = 3.23^(a)) IV-41 (4-) Br —

OC₂H₅ logP = 3.02^(a)) IV-42 (4-) Cl —

OC₂H₅ logP = 3.31^(a)) IV-43 (4-) Cl —

OC₂H₅ logP = 3.31^(a)) IV-44 (4-) Cl —

OC₂H₅ logP = 3.14^(a)) IV-45 (4-) NO₂ —

OC₂H₅ logP = 2.42^(a)) IV-46 (4-) NO₂ —

OC₂H₅ logP = 2.82^(a)) IV-47 (4-) CF₃ —

OC₂H₅ logP = 3.48^(a)) IV-48 (4-) CF₃ —

OC₂H₅ logP = 3.38^(a)) IV-49 (4-) CF₃ —

OC₂H₅ logP = 3.02^(a)) IV-50 (4-) CF₃ —

OC₃H₇ logP = 3.91^(a)) IV-51 (4-) OCH₃ —

OC₂H₅ IV-52 (4-) OCH₃ —

OC₂H₅ IV-53 (4-) CF₃ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.37 ppm. IV-54 (4-) CF₃ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.37 ppm. IV-55 — —

OC₂H₅ IV-56 — —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.37 ppm. IV-57 — —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.40 ppm. IV-58 (4-) Br —

OC₂H₅ logP = 2.95^(a)) IV-59 (4-) Br —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.31 ppm. IV-60 (4-) Br —

OC₂H₅ logP = 2.44^(a)) IV-61 (4-) F —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.35 ppm. IV-62 (4-) F —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.53 ppm. IV-63 (4-) F —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.40 ppm. IV-64 (4-) F —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.36 ppm. IV-65 (4-) Br —

OC₂H₅ logP = 3.34^(a)) IV-66 (4-) Br —

OC₂H₅ logP = 3.38^(a)) IV-67 (4-) Br —

OC₂H₅ logP = 3.31^(a)) IV-68 (4-) Br —

OC₂H₅ logP = 2.16^(a)) IV-69 (4-) Br —

OC₂H₅ logP = 2.41^(a)) IV-70 (4-) CF₃ —

OC₂H₅ logP = 3.51^(a)) IV-71 (4-) CF₃ —

OC₂H₅ logP = 3.54^(a)) IV-72 (4-) Br —

OC₂H₅ logP = 2.36^(a)) IV-73 (4-) Br —

OC₂H₅ logP = 2.88^(a)) IV-74 (4-) CF₃ —

OC₂H₅ logP = 2.68^(a)) IV-75 (4-) Br —

OC₂H₅ logP = 2.80^(a)) IV-76 (4-) CF₃ —

OC₂H₅ logP = 3.87^(a)) IV-77 (4-) CF₃ —

OC₂H₅ logP = 2.88^(a)) IV-78 (4-) CF₃ —

OC₂H₅ logP = 2.60^(a)) IV-79 (4-) CF₃ —

OC₂H₅ logP = 3.35^(a)) IV-80 (4-) Br —

OC₂H₅ logP = 2.86^(a)) IV-81 (4-) Cl —

OC₂H₅ logP = 2.83^(a)) IV-82 (4-) Br —

OC₂H₅ logP = 2.60^(a)) IV-83 (4-) CF₃ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.36 ppm. IV-84 (4-) CF₃ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.37 ppm. IV-85 (4-) CF₃ —

OC₂H₅ logP = 2.79^(a)) IV-86 (4-) CF₃ —

OC₂H₅ logP = 3.67^(a)) IV-87 (4-) CF₃ —

OC₂H₅ logP = 3.80^(a)) IV-88 (3-) CH₃ —

OC₂H₅ logP = 2.54^(a)) IV-89 (4-) SO₂CH₃ —

OC₂H₅ logP = 1.82^(a)) IV-90 (4-) CF₃ —

OC₂H₅ logP = 2.93^(a)) IV-91 (4-) CF₃ —

OC₂H₅ logP = 3.08^(a)) IV-92 (4-) CF₃ —

OC₂H₅ logP = 3.04^(a)) IV-93 (4-) CF₃ —

OC₂H₅ logP = 3.45^(a)) IV-94 (4-) F —

OC₂H₅ logP = 2.21^(a)) IV-95 (4-) F —

OC₂H₅ logP = 2.96^(a)) IV-96 (4-) F —

OC₂H₅ logP = 2.05^(a)) IV-97 (4-) F —

OC₂H₅ logP = 2.50^(a)) IV-98 (4-) F —

OC₂H₅ logP = 2.89^(a)) IV-99 (4-) CF₃ —

OC₂H₅ logP = 2.91^(a)) IV-100 (4-) Cl —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.39 ppm. IV-101 (4-) Cl —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.50 ppm. IV-102 (4-) Cl —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.49 ppm. IV-103 (4-) CF₃ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.29 ppm. IV-104 (4-) CF₃ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.53 ppm. IV-105 (4-) CF₃ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.34 ppm. IV-106 (4-) SO₂CH₃ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.39 ppm. IV-107 (4-) SO₂CH₃ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.43 ppm. IV-108 (4-) SO₂CH₃ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.40 ppm. IV-109 (4-) SO₂CH₃ —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.38 ppm. IV-110 (4-) Br —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.49 ppm. IV-111 — —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.3 ppm. IV-112 — —

OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.44 ppm. IV-113 (4-) CF₃ —

OC₂H₅ logP = 2.58^(a)) IV-114 (4-) SO₂CH₃ —

OCH₃ logP = 1.53^(a)) IV-115 (4-) SO₂CH₃ —

OCH₃ logP = 1.59^(a)) IV-116 (4-) I —

OCH₃ logP = 2.68^(a)) IV-117 (4-) CF₃ —

OCH₃ logP = 2.74^(a)) IV-118 (4-) CF₃ —

OCH₃ logP = 2.65^(a)) IV-119 (4-) CF₃ —

OC₂H₅ logP = 2.96^(a)) IV-120 — —

OCH₃ m.p.: 106° C.

[0217] The logP values given in Tables 4 were determined in accordancewith EEC Directive 79/931 Annex V.A8 by HPLC (High Performance LiquidChromatography) on a reversed-phase column (C 18). Temperature: 43° C.

[0218] (a) Mobile phases for the determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10%acetonitrile to 90% acetonitrile—corresponding measurement results inTable 1 are marked ^(a)).

[0219] (b) Mobile phases for the determination in the neutral range:0.01 molar aqueous phosphate buffer solution, acetonitrile; lineargradient from 10% acetonitrile to 90% acetonitrile—correspondingmeasurement results in Table 1 are marked ^(b)).

[0220] Calibration was carried out using unbranched alkan-2-ones (having3 to 16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones).

[0221] The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

USE EXAMPLES Example A

[0222] Pre-emergence Test

[0223] Solvent: 5 parts by weight of acetone

[0224] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0225] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0226] Seeds of the test plants are sown in normal soil. After about 24hours, the soil is sprayed with the preparation of active compound suchthat the particular amount of active compound is applied per unit area.The concentration of the spray liquor is chosen such that the particularamount of active compound desired is applied in 1000 liters of water perhectare.

[0227] After three weeks, the degree of damage to plants is rated in %damage in comparison to the development of the untreated control.

[0228] The figures denote:

[0229] 0%=no effect (like untreated control)

[0230] 100%=total destruction

[0231] In this test, for example, the compounds of Preparation Example 2and 3 exhibit strong activity against weeds, and they are tolerated wellby crop plants such as, for example, corn.

Example B

[0232] Post-emergence Test

[0233] Solvent: 5 parts by weight of acetone

[0234] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0235] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0236] Test plants of a height of 5-15 cm are sprayed with thepreparation of active compound such that the particular amounts ofactive compound are applied per unit area. The concentration of thespray liquor is chosen such that the particular amounts of activecompound desired are applied in 1000 l of water/ha.

[0237] After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control.

[0238] The figures denote:

[0239] 0%=no effect (like untreated control)

[0240] 100%=total destruction

[0241] In this test, for example, the compound of Preparation Example 2and 3 exhibit strong activity against weeds.

1. (Cancelled).
 2. A substituted benzoylpyrazole of the formula (I),

in which n represents the numbers 0, 1 or 2, A represents a single bondor represents alkanediyl (alkylene) having 1 to 4 carbon atoms, R¹represents optionally cyano-, carboxyl-, carbamoyl-, halogen-,C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl-, C₁-C₄-alkoxy-carbonyl-,C₁-C₄-alkylthio-, C₁-C₄-alkylsulfinyl- orC₁-C₄-alkylsulfonyl-substituted alkyl having 1 to 6 carbon atoms,represents in each case optionally cyano-, carboxyl-, carbamoyl-,halogen- or C₁-C₄-alkoxycarbonyl-substituted alkenyl or alkinyl havingin each case 2 to 6 carbon atoms, or represents optionally cyano-,carboxyl-, carbamoyl-, halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms,R² represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen,represents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl, alkoxy or alkoxycarbonyl having in eachcase up to 6 carbon atoms, represents optionally halogen-substitutedalkylthio having 1 to 6 carbon atoms, or represents optionally cyano-,halogen- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbonatoms, R³ represents hydrogen, nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, halogen, represents in each case optionally halogen,C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulfinyl- orC₁-C₄-alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinylor alkylsulfonyl having in each case up to 4 carbon atoms in the alkylgroups, or represents alkylamino, dialkylamino or dialkylaminosulfonylhaving in each case up to 4 carbon atoms in the alkyl groups, R⁴represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen,represents in each case optionally halogen-, C₁-C₄-alkoxy-,C₁-C₄-alkylthio-, C₁-C₄-alkylsulfinyl- orC₁-C₄-alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinylor alkylsulfonyl having in each case up to 4 carbon atoms in the alkylgroups, or represents alkylamino, dialkylamino or dialkylaminosulfonylhaving in each case up to 4 carbon atoms in the alkyl groups, Yrepresents hydrogen, represents in each case optionally cyano-,carboxyl-, carbamoyl-, halogen- or C₁-C₄-alkoxycarbonyl-substitutedalkyl, alkylcarbonyl or alkoxycarbonyl having in each case up to 6carbon atoms, represents in each case optionally halogen-substitutedalkylsulfonyl, alkylaminocarbonyl or dialkylaminocarbonyl having in eachcase up to 6 carbon atoms in the alkyl groups, represents in each caseoptionally cyano-, carboxyl-, carbamoyl-, halogen- orC₁-C₄-alkoxycarbonyl-substituted alkenyl, alkenylcarbonyl, alkinyl oralkinylcarbonyl having in each case 2 to 6 carbon atoms, representsoptionally halogen-substituted alkenylsulfonyl having up to 6 carbonatoms represents in each case optionally cyano-, halogen- orC₁-C₄-alkyl-substituted cycloalkyl, cycloalkylcarbonyl orcycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl groups and optionally 1 to 3 carbon atoms in the alkylmoiety, or represents in each case optionally nitro-, cyano-, carboyl-,carbamoyl-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁C₄-alkoxy-or C₁-C₄-halogenoalkoxy-substituted phenylcarbonyl, phenylsulfonyl,phenyl-C₁-C₄-alkyl or phenylcarbonyl-C₁-C₄-alkyl, and Z represents oneof the heterocyclic groupings below

in which in each case the broken bond is a single bond or a double bond,Q represents oxygen or sulfur, R⁵ represents hydrogen, hydroxyl,mercapto, cyano, halogen, represents in each case optionally cyano-,halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulfinyl- orC₁-C₄-alkylsulfonyl-substituted alkyl, alkylcarbonyl, alkoxy,alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl having in eachcase up to 6 carbon atoms in the alkyl groups, representspropadienylthio, represents in each case optionally halogen-substitutedalkylamino or dialkylamino having in each case up to 6 carbon atoms inthe alkyl groups, represents in each case optionally halogen-substitutedalkenyl, alkinyl, alkenyloxy, alkenylthio or alkenylamino having in eachcase up to 6 carbon atoms in the alkenyl or alkinyl groups, representsin each case optionally halogen-substituted cycloalkyl, cycloalkyloxy,cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy,cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6carbon atoms in the cycloalkyl groups and optionally up to 4 carbonatoms in the alkyl moiety, represents in each case optionally halogen-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted phenyl, phenyloxy, phenylthio,phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, representspyrrolidino, piperidino or morpholino, or—if two adjacent radicals R⁵and R⁵ are located on a double bond—together with the adjacent radicalR⁵ also represents a benzo grouping, and R⁶ represents hydrogen,hydroxyl, amino, alkylideneamino having up to 4 carbon atoms, representsin each case optionally halogen- or C₁-C₄-alkoxy-substituted alkyl,alkoxy, alkylamino, dialkylamino or alkanoylamino having in each case upto 6 carbon atoms in the alkyl groups, represents in each caseoptionally halogen-substituted alkenyl, alkinyl or alkenyloxy having ineach case up to 6 carbon atoms in the alkenyl or alkinyl groups,represents in each case optionally halogen-substituted cycloalkyl,cycloalkylalkyl or cycloalkylamino having in each case 3 to 6 carbonatoms in the cycloalkyl groups and optionally up to 3 carbon atoms inthe alkyl moiety, or represents in each case optionally halogen-,C₁-4-alkyl- or C₁-C₄-alkoxy-substituted phenyl or benzyl, or togetherwith an adjacent radical R⁵ or R⁶ represents optionally halogen- orC₁-C₄-alkyl-substituted alkanediyl having 3 to 5 carbon atoms, where theindividual radicals R⁵ and R⁶—if a plurality of these are attached tothe same heterocyclic groupings, may have identical or differentmeanings within the scope of the above definition.
 3. The compoundaccording to claim 2, wherein n represents the numbers 0 or 1, Arepresents a single bond, methylene, ethylidene (ethane-1,1-diyl) ordimethylene (ethane-1,2-diyl), R¹ represents in each case optionallyfluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-,ethylthio-, n- or i-propylthio-, methylsulfinyl-, ethylsulfinyl-, n- ori-propylsulfinyl-, methylsulfonyl-, ethylsulfonyl-, n- ori-propylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, represents in each case optionally fluorine-, chlorine- orbromine-substituted propenyl, butenyl, propinyl or butinyl, orrepresents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl, R² represents hydrogen, cyano, carbamoyl,thiocarbamoyl, represents in each case optionally cyano-, fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, represents ineach case optionally fluorine- and/or chlorine-substituted methylthio,ethylthio, n- or i-propylthio, or represents in each case optionallycyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, R³ representshydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine,chlorine, bromine, iodine, represents in each case optionally fluorine-and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-,ethylthio-, n- or i-propylthio-, methylsulfinyl-, ethylsulfinyl-,methylsulfonyl- or ethylsulfonyl-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, represents in each case optionallyfluorine- and/or chlorine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, represents ineach case optionally fluorine- and/or chlorine-substituted methylthio,ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- ori-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl,or represents methylamino, ethylamino, n- or i-propylamino,dimethylamino, diethylamino, dimethylaminosulfonyl ordiethylaminosulfonyl, R⁴ represents nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, fluorine, chlorine, bromine, represents in each caseoptionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- orethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, represents in each case optionally fluorine- and/or chlorine-,methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- ori-propoxy, represents in each case optionally fluorine- and/orchlorine-substituted methylthio, ethylthio, n- or i-propylthio,methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl,ethylsulfonyl, n- or i-propylsulfonyl, or represents methylamino,ethylamino, n- or i-propylamino, dimethylamino, diethylamino,dimethylaminosulfonyl or diethylaminosulfonyl, R⁵ represents hydrogen,hydroxyl, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl,trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl,fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, fluoro-n-propyl,fluoro-i-propyl, chloro-n-propyl, chloro-i-propyl, methoxymethyl,ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, fluoroethoxy, chloroethoxy,difluoroethoxy, dichloroethoxy, trifluoroethoxy, trich loroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy, fluorodichloroethoxy,methylthio, ethylthio, n- or i-propylthio, fluoroethylthio,chloroethylthio, difluoroethylthio, dichloroethylthio,chlorofluoroethylthio, chlorodifluoroethylthio, fluorodichloroethylthio,methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl,ethylsulfonyl, n- or i-propylsulfonyl, dimethylamino, propenylthio,butenylthio, propinylthio, butinylthio, cyclopropyl, cyclopropylmethyl,cyclopropylmethoxy, phenyl or phenoxy, R⁶ represents amino, methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy,methylamino, dimethylamino, cyclopropyl or cyclopropylmethyl, ortogether with R⁵ represents propane-1,3-diyl (trimethylene),butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl (pentamethylene),and Y represents hydrogen, represents in each case optionally cyano-,fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl orethoxycarbonyl, represents in each case optionally fluorine-, chlorine-and/or bromine-substituted methylsulfonyl-, ethylsulfonyl-, n- ori-propylsulfonyl-, n-, i-, s- or t-butylsulfonyl-, methylaminocarbonyl,ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonylor diethylaminocarbonyl, represents in each case optionally fluorine-,chlorine- or bromine-substituted propenyl, butenyl, propenylcarbonyl,butenylcarbonyl, propenylsulfonyl, butenylsulfonyl, propinyl, butinyl,propinylcarbonyl or butinylcarbonyl, represents in each case optionallycyano-, fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylcarbonyl,cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or-propoxy-, difluoromethoxy- or trifluoromethoxy-substitutedphenylcarbonyl, phenylsulfonyl, benzyl or phenylcarbonylmethyl. 4.(Cancelled)
 5. The compound according to claim 2, wherein Q representsoxygen.
 6. The compound according to claim 2 wherein n represents
 0. 7.A process for preparing a compound according to claim 2 comprising: (a)reacting a pyrazole of the formula (II)

in which R¹, R² and Y are as defined in claim 2, with a substitutedbenzoic acid of the formula (Ill),

in which n, A, R³, R⁴ and Z are as defined in claim 2, in the presenceof a dehydrating agent, optionally in the presence of one or morereaction auxiliaries and optionally in the presence of a diluent, or (b)reacting a pyrazole of the formula (II)

in which R¹, R² and Y are as defined in claim 2, with a member selectedfrom the group consisting of a substituted benzoic acid derivative ofthe formula (IV)

in which n, A, R³, R⁴ and Z are as defined in claim 2, and X representscyano, halogen or alkoxy, and corresponding carboxylic anhydridesthereof optionally in the presence of one or more reaction auxiliariesand optionally in the presence of a diluent, or (c) reacting asubstituted benzoylpyrazole of the formula (Ia)

in which n, A, R¹, R², R³, R⁴ and Z are as defined in claim 2, with acompound of the formula (V) H—Y  (V) in which Y is as defined in claim2, except for hydrogen, and optionally further comprising the step ofincluding as a reactant corresponding isocyanates or isothiocyanatesthereof optionally in the presence of one or more reaction auxiliariesand optionally in the presence of a diluent, and, optionally furthercomprising the step of subjecting the resulting compound of the formula(I) to one or more reactions selected from the group consisting of anelectrophilic reaction, a nucleophilic reaction, an oxidation reaction,a reduction reaction and combinations thereof within the scope of thedefinition of the substituents, or further comprising the step ofconverting the compound of the formula (I) into a salt.
 8. A compound ofthe formula (Ia)

in which n, A, R¹, R², R³, R⁴ and Z are as defined in claim
 2. 9. Anherbicidal composition, comprising at least one of the compoundsaccording to claim 2 and an extender.
 10. A method for controllingundesirable plants comprising the step of applying an herbicidallyeffective amount of at least one compound according to claim 2 to amember selected from the group consisting of said plant and a habitat ofsaid plant.